Name: 1485-07-0|2-(Naphthalen-2-yl)ethanol|95%
Brand: Ambeed
SKU: A218419
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1
[ 1485-07-0 ]
[ 2086-62-6 ]

Yield	Reaction Conditions	Operation in experiment
83%	With pyridine; phosphorus tribromide In benzene for 6h; Ambient temperature;
82%	With hydrogen bromide for 3h; Reflux;
73%	With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 1h;

72%	With 1H-imidazole; N-Bromosuccinimide; triphenylphosphine In dichloromethane at 20℃; for 24h;	30.2 Step 2: 2-(2-bromoethyl)naphthalene A solution of triphenylphosphine (4.72 g, 18 mmol, 1.3 eq.) and A-bromosuccinimide (3.2 g, 18 mmol, 1.3 eq.) in anhydrous DCM (45 mL) was stirred for 10 minutes. The product obtained in the previous step (2.33 g, 13.5 mmol, 1.0 eq.) was added, followed immediately by imidazole (919 mg, 13.5 mmol, 1.0 eq.) and the mixture was stirred at room temperature for 24 hours. The reaction mixture was partitioned between H2O and DCM and the aqueous layer was extracted with DCM (three times). The combined organic extracts was dried over Na2S04, filtered and evaporated to dryness. The crude residue was purified by column chromatography to give the expected compound (2.3 g, 72 %) as a white solid. (0820) NMR (CDC , 500 MHz) d (ppm): 7.83-7.80 (m, 3H); 7.67 (br s, 1H); 7.50-7.44 (m, 2H); 7.34 (dd, 1H, J = 8.0 and 1.5 Hz); 3.66 (t, 2H, J = 7.5 Hz); 3.34 (t, 2H, J = 7.5 Hz)
71%	With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃; for 2.16667h;	2 Step 2: Preparation of 2-(2-bromoethyl)naphthalene To a solution of 2-(naphthalen-2-yl)ethan-1-ol (5.20 g, 30.2 mmol) in DCM (100 mL), CBr4 (10.99 g, 33.21 mmol) and PPh3 (8.70 g, 33.2 mmol) were added portionwise at 0°C. The reaction mixture was stirred for 10 minutes, then the temperature was raised to room temperature and maintained for 2 hours. After complete consumption of thestarting material as determined by TLC, ice-cold water was added into the reaction mixture, which was then extracted with DCM. The combined organic layers were washed with water, then brine solution, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude product. The crude compound was purified by flash column chromatography using 10-15% Ethyl acetate in petroleum ether as aneluent, to give 2-(2-bromoethyl)naphthalene as a yellow liquid (5.2 g, 71 %).
	With sulfuric acid; hydrogen bromide
	With phosphorus tribromide; benzene
	With hydrogen bromide
	With phosphorus tribromide In tetrachloromethane
	With triphenylphosphine In N-Bromosuccinimide; hexane; benzene	7 Preparation 7 Preparation 7 2-(2-bromoethyl)naphthalene STR14 To a solution of 25 g (145 mmole) of 2-(2-naphthyl)ethanol and 67.9 g (259 mmole) of triphenylphosphine in 200 ml of benzene was added in portions 46.1 g (259 mmole) of N-bromosuccinimide. A temperature of 45°-50° was maintained by cooling the reaction mixture as needed in an ice bath. After the mixture was poured into 750 ml of hexane and filtered, the filtrate was diluted with an additional 400 ml of hexane and allowed to stand overnight. The solution was concentrated to dryness and the resultant solid was purified by chromatography on silica gel. The title compound (30.5 g), m.p. 55°-57°, was homogeneous by thin-layer chromatography (5%, 10%, and 15% by volume ethyl acetate-hexane on silica gel plates), and was used in subsequent reactions without further purification.

Reference： [1]Novak, Lajos; Rohaly, Janos; Poppe, Laszlo; Hornyanszky, Gabor; Kolonits, Pal; et al. [Liebigs Annalen der Chemie, 1992, # 2, p. 145 - 158]
[2]Banks, Tony M.; Clay, Samuel F.; Glover, Stephen A.; Schumacher, Rhiannon R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 15, p. 3699 - 3714]
[3]Nishizawa, Seiichi; Cui, Ying-Yu; Minagawa, Masakazu; Morita, Kotaro; Kato, Yuichi; Taniguchi, Shinichiro; Kato, Ryo; Teramae, Norio [Journal of the Chemical Society. Perkin Transactions 2 (2001), 2002, # 5, p. 866 - 870]
[4]Current Patent Assignee: NATIONAL INSTITUTE OF HEALTH AND MEDICAL RESEARCH; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; QUANTUM GENOMICS; COLLEGE DE FRANCE - WO2020/84131, 2020, A1 Location in patent: Page/Page column 70
[5]Current Patent Assignee: NOVOGEN LTD - WO2016/8011, 2016, A1 Location in patent: Page/Page column 58; 59
[6]Tatewosjan; Babajan [Zhurnal Obshchei Khimii, 1952, vol. 22, p. 1421,1426; engl. Ausg. S. 1465, 1469]
[7]Karrer et al. [Helvetica Chimica Acta, 1940, vol. 23, p. 585,586]
[8]Cagniant,P. et al. [Bulletin de la Societe Chimique de France, 1961, p. 1934 - 1937] Campaigne,E.; Heaton,B.G. [Journal of Organic Chemistry, 1964, vol. 29, p. 2372 - 2378]
[9]Mitra,A.K. et al. [Journal of the Indian Chemical Society, 1971, vol. 48, p. 391 - 394]
[10]Current Patent Assignee: PFIZER INC - US4644071, 1987, A

2
[ 581-96-4 ]
[ 1485-07-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;	30.1 Step 1: 2-(naphthalen-2-yl)ethan-l-ol At 0°C, a solution of 2-naphthylacetic acid (5.0 g, 26.85 mmol, 1.0 eq.) in anhydrous THF (13 mL) was added dropwise to a lithium aluminium hydride solution (2 M solution in THF, 27 mL, 53.70 mmol, 2.0 eq.) in anhydrous THF (13 mL) under argon atmosphere. The reaction was exothermic and the mixture became yellow. The reaction mixture was stirred for 2 h at room temperature, cooled to 0°C and then quenched slowly with 2 mL of H2O. An aqueous solution of NaOH (4 mL, 15%) and H2O (6 mL) were successively added and the mixture was stirred for 15 min. Anhydrous Na2S04 was added and the mixture was stirred for 15 min. The yellow mixture was filtered over a pad of celite and the filtrate was concentrated under vacuum to give the expected compound (4.5 g, 97%) as a yellow powder. (0818) NMR (CDCI3, 500 MHz) d (ppm): 7.83-7.79 (m, 3H); 7.69 (t, 1H, J = 1.0 Hz); 7.49-7.43 (m, 2H); 7.37 (dd, 1H, J = 8.0 and 1.5 Hz); 3.96 (t, 2H, J = 6.5 Hz); 3.04 (t, 2H, J = 6.5 Hz)
89%	With lithium aluminium tetrahydride In diethyl ether Reflux;
85%	With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 12h; Schlenk technique;

60%	Stage #1: 2-naphthylacetic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h; Stage #2: With sodium tetrahydroborate; water In tetrahydrofuran at 0℃; for 0.5h;
43%	With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 0.5h;
	With lithium aluminium tetrahydride; diethyl ether
	With lithium aluminium tetrahydride
	With lithium aluminium tetrahydride In diethyl ether
	With lithium aluminium tetrahydride In tetrahydrofuran
	With diborane In tetrahydrofuran
	With lithium aluminium tetrahydride In diethyl ether for 2h;	2; 3 Commercially available 2-naphthylacetic acid (3 g, 16.1 mmol) m 8 mL of anhydrous diethyl ether was added dropwise to a solution of lithium aluminum hydride (1.2 g, 32.2 mmol) in 8 mL of anhydrous diethyl ether under nitrogen atmosphere. The reaction mixture was aged for 2 h, quenched with aqueous Rochelle salt, stirred for an additional 2 h, partitioned between saturated aqueous NaHCO3 and diethyl ether, the organic phase was separated and dried over anhydrous sodium sulfate, and then evaporated under reduced pressure to provide the crude alcohol product (1.4 g). This alcohol (1.0 g, 5.81 mmol) was oxidized directly with iodobenzene diacetate (2.1 g, 6.5 mmol) and catalytic TEMPO (10%) in methylene chloride solvent (20 mL). The reaction mixture was quenched with aqueous sodium thiosulfate, partitioned with methylene chloride, the organic phase washed with aqueous NaHCO3, and the organic phase concentrated in vacuo to provide the clean aldehyde product. This crude aldehyde intermediate (500 mg, 2.9 mmol) was combined with methyl (triphenylphosphoranyhdene) acetate (1.47 g, 4.4 mmol) in toluene (10 mL), and the reaction mixture heated at reflux for 4 h. The mixture was concentrated in vacuo to a residue which was purified by flash column chromatography (S1O2, EtOAc/hexanes) to give the desired methyl enoate. This intermediate was then dissolved in tetrahydrofuran (10 mL), treated with aqueous 1N NaOH (5 mL), refluxed for 2 h, the mixture cooled, acidified and extracted with ethyl acetate. The organic phase was concentrated in vacuo to provide the enoic acid, which was treated with catalytic palladium on carbon in methanol (20 mL), and hydrogenated at 1 atmosphere with a hydrogen-filled balloon for 12 h. The reaction mixture was filtered over celite and concentrated in vacuo to provide the clean crude acid defined as Compound A in Scheme 2. Compound A (50 mg, 0.234 mmol) was converted into EXAMPLE 3 in a similar manner as m EXAMPLE 1 and illustrated in Scheme 1 using anthranihc acid directly in the amide coupling reaction The product Was purified via preparative RPHPLC and then recrystallization (diethyl ether/hexane) to give the desired product. 1H NMR (CDCl3, 500 MHz) δ 10.93 (s, 1H), 8 79 (d, 1H), 8.11 (d, 1H), 7.80(m, 3H), 7.68(s, 1H), 7.61(t, 1H), 7.40(m, 2H), 7.38 (d, 1H), 7.12 (t, 1H), 2.92 (t, 2H), 2.53 (t, 2H), 2.22 (m, 2H); LCMS m/z 332 (M+-1).
	Multi-step reaction with 2 steps 1: sulfuric acid / 3 h / Reflux 2: diisobutylaluminium hydride / tetrahydrofuran; toluene / 20 °C
	With dimethylsulfide borane complex In tetrahydrofuran for 1h; Inert atmosphere; Reflux;
	With diborane In tetrahydrofuran; water at 0 - 20℃; for 2h; Inert atmosphere;	161 Synthesis of Compound 161.2. Example 161 Synthesis of ethyl 3-(2-hydroxyethyl)-5-methyl-1-[2-(naphthalen-2-yl)ethyl]-2,4-dioxo-1H,2H,3H,4H-thieno[2,3-d]pyrimidine-6-carboxylate (I-30) Synthesis of Compound 161.2. Into a 250-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed 161.1 (7.44 g, 39.96 mmol, 1.00 equiv) and tetrahydrofuran (80 mL). This was followed by the addition of BH3/THF (1 M) (80 mL) dropwise with stirring at 0° C. The resulting solution was stirred for 2 h at room temperature. The reaction was then quenched by the addition of 20 mL of water. The resulting solution was extracted with 2*150 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 7.05 g (crude) of 161.2 as a colorless oil.
	With lithium aluminium tetrahydride In tetrahydrofuran at -78 - 20℃;
	With borane-THF In tetrahydrofuran at 0℃; for 1.16667h; Inert atmosphere;	12.1 Step 1: Preparation of 2-(naphthalen-2-yl)ethan-1-ol BH3•THF (16.1 mL, 1M in THF) was added dropwise into a mixture of 2- (naphthalen-2-yl)acetic acid (300 mg, 1.61 mmol), tetrahydrofuran (10 mL), at 0°C in 10 min under nitrogen. The resulting solution was stirred for lh at 0°C in a water/ice bath. The reaction was then quenched by water, extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. This resulted in the title compound (1 g, crude) as an off- white solid, which was used for the next step without any further purification.
	With lithium aluminium tetrahydride In diethyl ether at 20℃; Inert atmosphere;	2-(2-Iodoethyl)naphthalene (4n) 2-Naphthylacetic acid (2.5 g, 13 mmol) in Et2O (56 mL) was added slowly to LAH (1.0 g, 27 mmol) in Et2O (11 ml) and the mixture was stirred for 15 min at r.t. The crude reaction mixture was quenched by adding H2O (1 mL), 15% aq NaOH (1 mL), and H2O (3 mL) sequentially. The resulting white solid was removed by filtering through a Celite pad (EtOAc). The organic layer was separated and dried over Na2SO4. After removal of the solvent, the crude product was purified by Yamazen YFLC AI-580 using Universal Column SiOH (hexane/EtOAc) to afford crude 2-(2-naphthyl)ethan-1-ol (2.1 g) as a white solid. According to general procedure A, the crude alcohol (2.1 g, ca. 12 mmol) was treated with iodine (3.4 g, 13 mmol), PPh3 (3.5 g, 13 mmol), and imidazole (990 mg, 15 mmol). The crude product was purified by Yamazen YFLC AI-580 using Universal Column SiOH (hexane/EtOAc) to provide 4n. Yield: 2.0 g, 6.9 mmol (52% over 2 steps); white solid; mp 71-72 °C; Rf = 0.50 (hexane/EtOAc 9:1, UV). NMR spectra of the obtained product were consistent with the reported data.31 1H NMR (400 MHz, CDCl3): δ = 7.83-7.78 (m, 3 H), 7.65 (s, 1 H), 7.49-7.44 (m, 2 H), 7.32 (dd, J = 8.3, 1.6 Hz, 1 H), 3.44 (t, J = 7.4 Hz, 2 H), 3.34 (t, J = 7.4 Hz, 2 H). 13C NMR (100 MHz, CDCl3): δ = 138.0, 133.5, 132.3, 128.3, 127.7, 127.6, 126.9, 126.5, 126.2, 125.6, 40.4, 5.4.

Reference： [1]Current Patent Assignee: NATIONAL INSTITUTE OF HEALTH AND MEDICAL RESEARCH; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; QUANTUM GENOMICS; COLLEGE DE FRANCE - WO2020/84131, 2020, A1 Location in patent: Page/Page column 69
[2]Banks, Tony M.; Clay, Samuel F.; Glover, Stephen A.; Schumacher, Rhiannon R. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 15, p. 3699 - 3714]
[3]Mayr, Stefanie; Marin-Luna, Marta; Zipse, Hendrik [Journal of Organic Chemistry, 2021, vol. 86, # 4, p. 3456 - 3489]
[4]Location in patent: experimental part Morales-Serna, Jose Antonio; Garcia-Rios, Erendira; Bernal, Jorge; Paleo, Ehecatl; Gavino, Ruben; Cardenas, Jorge [Synthesis, 2011, # 9, p. 1375 - 1382]
[5]Nishizawa, Seiichi; Cui, Ying-Yu; Minagawa, Masakazu; Morita, Kotaro; Kato, Yuichi; Taniguchi, Shinichiro; Kato, Ryo; Teramae, Norio [Journal of the Chemical Society. Perkin Transactions 2 (2001), 2002, # 5, p. 866 - 870]
[6]Lawesson [Acta Chemica Scandinavica (1947), 1958, vol. 12, p. 1,7]
[7]Schadt,F.L. et al. [Journal of the American Chemical Society, 1978, vol. 100, p. 228 - 246]
[8]Mitra,A.K. et al. [Journal of the Indian Chemical Society, 1971, vol. 48, p. 391 - 394] Liang, Jiang-Lin; Yuan, Shi-Xue; Huang, Jie-Sheng; Che, Chi-Ming [Journal of Organic Chemistry, 2004, vol. 69, # 11, p. 3610 - 3619]
[9]Campaigne,E.; Heaton,B.G. [Journal of Organic Chemistry, 1964, vol. 29, p. 2372 - 2378]
[10]Gilbert, Andrew; Heath, Peter; Kashoulis-Koupparis, Annoula; Ellis-Davies, Graham C. R.; Firth, Susan M. [Journal of the Chemical Society. Perkin transactions I, 1988, p. 31 - 36]
[11]Current Patent Assignee: MERCK & CO INC - WO2006/52555, 2006, A2 Location in patent: Page/Page column 26; 40-41
[12]Revelant, Germain; Dunand, Sandrine; Hesse, Stephanie; Kirsch, Gilbert [Synthesis, 2011, # 18, p. 2935 - 2940]
[13]Maity, Prantik; Srinivas, Harathi D.; Watson, Mary P. [Journal of the American Chemical Society, 2011, vol. 133, # 43, p. 17142 - 17145]
[14]Current Patent Assignee: GILEAD SCIENCES INC - US2013/123231, 2013, A1 Location in patent: Paragraph 1262; 1263; 1264
[15]Gising, Johan; Belfrage, Anna Karin; Alogheli, Hiba; Ehrenberg, Angelica; Åkerblom, Eva; Svensson, Richard; Artursson, Per; Karlén, Anders; Danielson, U. Helena; Larhed, Mats; Sandström, Anja [Journal of Medicinal Chemistry, 2014, vol. 57, # 5, p. 1790 - 1801]
[16]Current Patent Assignee: ROCHE HOLDING AG; PARAZA PHARMA INC - WO2018/96159, 2018, A1 Location in patent: Paragraph 0261-0264
[17]Kojima, Masahiro; Matsunaga, Shigeki [Synthesis, 2020, vol. 52, # 13, p. 1934 - 1946]

3
[ 110-87-2 ]
[ 1485-07-0 ]
2-(2-Naphthalen-2-yl-ethoxy)-tetrahydro-pyran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In dichloromethane for 5h;

Reference： [1]Olah, George A.; Husain, Altaf; Singh, Brij P. [Synthesis, 1983, # 11, p. 892 - 895]

4
[ 358-23-6 ]
[ 1485-07-0 ]
Trifluoro-methanesulfonic acid 2-naphthalen-2-yl-ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane
	With 2,6-dimethylpyridine In dichloromethane at -78℃; Inert atmosphere;

Reference： [1]Berkowitz, David B.; Eggen, MariJean; Shen, Quanrong; Sloss, Darby G. [Journal of Organic Chemistry, 1993, vol. 58, # 23, p. 6174 - 6176]
[2]Mallick, Shubhadip; Würthwein, Ernst-Ulrich; Studer, Armido [Organic Letters, 2020, vol. 22, # 16, p. 6568 - 6572]

5
[ 1485-07-0 ]
[ 109216-50-4 ]
[ 117873-89-9 ]

Yield	Reaction Conditions	Operation in experiment
89%	With dmap In dichloromethane Heating;
86.8%	With dmap In pyridine; dichloromethane for 5h; Heating;

Reference： [1]Park, Tae Kyo; Schroeder, Joseph; Rebek Jr., Julius [Tetrahedron, 1991, vol. 47, # 14-15, p. 2507 - 2518]
[2]Askew; Ballester; Buhr; Jeong; Jones; Parris; Williams; Rebek Jr. [Journal of the American Chemical Society, 1989, vol. 111, # 3, p. 1082 - 1090]

6
[ 1485-07-0 ]
[ 130525-40-5 ]
[ 134456-93-2 ]

Yield	Reaction Conditions	Operation in experiment
	With dicyclohexyl-carbodiimide In dichloromethane at 0℃;

Reference： [1]Park, Tae Kyo; Schroeder, Joseph; Rebek Jr., Julius [Journal of the American Chemical Society, 1991, vol. 113, # 13, p. 5125 - 5127]

7
[ 1485-07-0 ]
[ 70080-13-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 0.916667h;
98%	With Dess-Martin periodane In dichloromethane for 2h;
83%	With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetonitrile at 80℃; for 2h;

70%	With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium bromide In ethyl acetate; toluene at 20℃;
57%	With Dess-Martin periodane In dichloromethane at 0 - 25℃; for 4h;
52%	With N-(tert-butyl)benzenesulfinimidoyl chloride; zinc(II) oxide In dichloromethane at -78℃; for 2h;
52%	With N-(tert-butyl)benzenesulfinimidoyl chloride; zinc(II) oxide In dichloromethane at -78℃; for 2h;
	With pyridine-SO₃ complex; dimethyl sulfoxide; triethylamine In dichloromethane at 20℃; for 2h;	38 Reference Example 38 Preparation method of 2-allylnaphthalene In an amount of 515.8 mg of 2-naphthaleneethanol was added with 30 ml of methylene chloride and dissolved therein, added with 6.3 ml of dimethyl sulfoxide, 2.5 ml of triethylamine, and 1.4 g of sulfur trioxide/pyridine complex, stirred at room temperature for 2 hours, then added with 50 ml of water, and extracted with 50 ml of ethyl acetate, and the organic layer was successively washed with 30 ml of saturated aqueous ammonium chloride, and 30 ml of saturated brine. The organic layer was dried over anhydrous sodium sulfate, and then filtered, and the filtrate was concentrated under reduced pressure to obtain 511 mg of 2-(naphthalen-2-yl)acetaldehyde.
	With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium bromide; sodium hydrogencarbonate In water; ethyl acetate; toluene at 0℃; for 1.16667h;	32 A solution of 2-naphthalen-2-yl-ethanol (1.02 g, 5.8 mmol), 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) (9 mg, 0.058 mmol) and sodium bromide (0.65 g, 6.4 mmol) in a mixture of toluene (18 mL), ethyl acetate (18 mL), and water (3mL) was cooled to 0 °C and added dropwise over 1 hour a solution containing the following: sodium hypochlorite (17.2 mL, 0.37 M, 6.4 mmol) and sodium hydrogencarbonate (1.46 g, 17.4 mmol). The reaction mixture was stirred at 0 °C for 10 min., and the phases separated. The aqueous layer was extracted with ethyl acetate (150 mL). The combined organic phases were washed with a solution of potassium iodone (0.2 g) in 10 % aqueous potassium hydrogensulfate (150 mL), water (150 mL), brine (150 mL), dried (MgSO4), filtered, and concentrated in vacuo to provide 980 mg of a 3:1 mixture of naphthalen-2-yl-acetaldehyde and 2-naphthalen-2-yl-ethanol. 1H-NMR (CDCl3): δ 9.81 (t, 1H, J = 1.5 Hz), 7.92-7.80 (m, 3H), 7.68 (bs, 1H), 7.55-7.42 (m, 3H), 3.87 (d, 2H, J = 1.5 Hz). To a solution of 2-amino-5-aminomethyl-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester (290 mg, 0.71 mmol) in 1,2-dichloroethane (3 ml) was added the above mixture of 2-naphthyl-acetaldehyde (100 mg, 0.59 mmol), sodium triacetoxyborohydride (190 mg, 0.88 mmol) and the mixture was stirred at room temperature under nitrogen for 2.5 hours. The crude reaction mixture was quenched with saturated sodium bicarbonate (50 ml) and the solution extracted with ethyl acetate (100 ml). The organic phase was dried (MgSO4), filtered, and concentrated in vacuo providing a foam, which was taken directly to the next step. LC-MS showed that 2-amino-6-(4-methoxy-benzyl)-5-((2-naphthalen-2-yl-ethylamino)-methyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester was the major component. LC-MS: m/z: 558.1 [M+H]+, Rf = 2.23 min. To a solution of 2-amino-6-(4-methoxy-benzyl)-5-((2-naphthalen-2-yl-ethylamino)methyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester in tetrahydrofuran (3 ml) was added di-tert-butyl-dicarbonate (188 mg, 0.85 mmol) and N,N-dimethylformamide (18 mg, 0.14 mmol). The reaction was stirred at room temperature for 7 hours under nitrogen. The crude reaction mixture was diluted with dichloromethane (50 ml) and washed with water (50 ml) and brine (50 ml). The organic phase was dried (MgSO4), filtered, and concentrated in vacuo affording a foam, which was used without further purification in the next step. LC-MS showed that 2-amino-5-((tert-butoxycarbonyl-(2-naphthalen-2-yl-ethyl)-amino)-methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester was the major component. Rf= 2.74, m/z: 658.1 [M+H]+, Calculated: 657.4. To crude 2-amino-5-((tert-butoxycarbonyl-(2-naphthalen-2-yl-ethyl)-amino)-methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester was added dichloromethane (5 ml) and imidazol-1-yl-oxo-acetic acid tert-butyl ester (400 mg, 1.78 mmol) and the reaction mixture stirred at room temperature for 12 hours. The crude reaction mixture was added to dichloromethane (50 ml) and washed with water (50 ml) and brine (50 ml). The organic phase was dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography using a mixture of dichloromethane/ethyl acetate (10:1) as eluent, which afforded 20.3 mg (39 % over tree steps) of 2-(tert-butoxyoxalyl-amino)-5-((tert-butoxycarbonyl-(2-naphthalen-2-yl-ethyl)-amino)methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester as a foam. 1H NMR (CDCl3) δ 7.99-7.92 (m, 3H), 7.88 (s, 1H), 7.68-7.57 (m, 3H), 7.45 (d, 2H, J = 7.8 Hz), 6.99 (d, 2H, J = 8.1 Hz), 3.90-3.75 (m, 7H), 3.56-3.42 (m, 5H), 3.19-3.13 (m, 2H), 2.88-2.82 (m, 2H), 1.79 (s, 9H), 1.71 (s, 18H); LC-MS: m/z: 786.2 [M+H]+, Rf = 3.03 min. To a solution of 2-(tert-butoxyoxalyl-amino)-5-((tert-butoxycarbonyl-(2-naphthalen-2-yl-ethyl)-amino)methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester (20 mg, 0.03 mmol) in dry dichloromethane (200 µl) at 0 °C was added 50 % trifluoroacetic acid in dichloromethane (2.5 ml). The reaction was stirred for 14 hours at room temperature and then concentrated in vacuo. The resultant solid was resuspended in dichloromethane, filtered, and dried in vacuo to provide 13 mg (90 %) of the title compound as a solid. 1H NMR (DMSO-d6) δ 9.15 (s, 1H), 8.09-8.01 (m, 3H), 7.93 (s, 1H), 7.68-7.57 (m, 3H), 7.45 (d, 2H, J =7.8 Hz), 6.99 (d, 2H, J = 8.1 Hz), 4.18-4.12 (m, 2H), 3.90-3.75 (m, 7H), 3.56-3.42 (m, 3H), 3.19-3.13 (m, 2H), 2.88-2.82 (m, 2H); LC-MS: m/z: 574.7 [M+H]+, Rf = 1.36 min.
	With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium bromide In water; ethyl acetate; toluene at 0℃; for 1.16667h;	96 Example 96 6-(4-Methoxy-benzyl)-5-((2-naphthalen-2-yl-ethylamino)methyl)-2-(oxalyl-amino)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid; A solution of 2-naphthalen-2-yl-ethanol (1.02 g, 5.8 mmol), 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) (9 mg, 0.058 mmol) and sodium bromide (0.65 g, 6.4 mmol) in a mixture of toluene (18 mL), ethyl acetate (18 mL), and water (3 mL) was cooled to 0° C. and added dropwise over 1 hour a solution containing the following: sodium hypochlorite (17.2 mL, 0.37 M, 6.4 mmol) and sodium hydrogencarbonate (1.46 g, 17.4 mmol). The reaction mixture was stirred at 0° C. for 10 min., and the phases separated. The aqueous layer was extracted with ethyl acetate (150 mL). The combined organic phases were washed with a solution of potassium iodone (0.2 g) in 10,% aqueous potassium hydrogensulfate (150 mL), water (150 mL), brine (150 mL), dried (MgSO4), filtered, and concentrated in vacuo to provide 980 mg of a 3:1 mixture of naphthalen-2-yl-acetaldehyde and 2-naphthalen-2-yl-ethanol.1H-NMR (CDCl3): δ 9.81 (t, 1H, J=1.5 Hz), 7.92-7.80 (m, 3H), 7.68 (bs, 1H), 7.55-7.42 (m, 3H), 3.87 (d, 2H, J=1.5 Hz).To a solution of 2-amino-5-aminomethyl-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester (290 mg, 0.71 mmol) in 1,2-dichloroethane (3 ml) was added the above mixture of 2-naphthyl-acetaldehyde (100 mg, 0.59 mmol), sodium triacetoxyborohydride (190 mg, 0.88 mmol) and the mixture was stirred at room temperature under nitrogen for 2.5 hours. The crude reaction mixture was quenched with saturated sodium bicarbonate (50 ml) and the solution extracted with ethyl acetate (100 ml). The organic phase was dried (MgSO4), filtered, and concentrated in vacuo providing a foam, which was taken directly to the next step. LC-MS showed that 2-amino-6-(4-methoxy-benzyl)-5-((2-naphthalen-2-yl-ethylamino)-methyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester was the major component.LC-MS: m/z: 558.1 [M+H]+, Rf=2.23 min.To a solution of 2-amino-6-(4-methoxy-benzyl)-5-((2-naphthalen-2-yl-ethylamino)methyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl-ester in tetrahydrofuran (3 ml) was added di-tert-butyl-dicarbonate (188 mg, 0.85 mmol) and N,N-dimethylformamide (18 mg, 0.14 mmol). The reaction was stirred at room temperature for 7 hours under nitrogen. The crude reaction mixture was diluted with dichloromethane (50 ml) and washed with water (50 ml) and brine-(50 ml). The organic phase was dried (MgSO4), filtered, and concentrated in vacuo affording a foam, which was used without further purification in the next step.LC-MS showed that 2-amino-5-((tert-butoxycarbonyl-(2-naphthalen-2-yl-ethyl)-amino)-methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester was the major component. Rf=2.74, m/z: 658.1 [M+H]+, Calculated: 657.4.To crude 2-amino-5-((tert-butoxycarbonyl-(2-naphthalen-2-yl-ethyl)-amino)-methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester was added dichloromethane (5 ml) and imidazol-1-yl-oxo-acetic acid tert-butyl ester (400 mg, 1.78 mmol) and the reaction mixture stirred at room temperature for 12 hours. The crude reaction mixture was added to dichloromethane (50 ml) and washed with water (50 ml) and brine (50 ml). The organic phase was dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography using a mixture of dichloromethane/ethyl acetate (10:1) as eluent; which afforded 20.3 mg (39% over tree steps) of 2-(tert-butoxyoxalyl-amino)-5-((tert-butoxycarbonyl-(2-naphthalen-2-yl-ethyl)-amino)methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester as a foam.1H NMR (CDCl3) δ 7.99-7.92 (m, 3H), 7.88 (s, 1H), 7.68-7.57 (m, 3H), 7.45 (d, 2H, J=7.8 Hz), 6.99 (d, 2H, J=8.1 Hz), 3.90-3.75 (m, 7H), 3.56-3.42 (m, 5H), 3.19-3.13 (m, 2H), 2.88-2.82 (m, 2H), 1.79 (s, 9H), 1.71 (s, 18H);LC-MS: m/z: 786.2 [M+H]+, Rf=3.03 min.To a solution of 2-(tert-butoxyoxalyl-amino)-5-((tert-butoxycarbonyl-(2-naphthalen-2-yl-ethyl)-amino)methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester (20 mg, 0.03 mmol) in dry dichloromethane (200 μl) at 0° C. was added 50% trifluoroacetic acid in dichloromethane (2.5 ml). The reaction was stirred for 14 hours at room temperature and then concentrated in vacuo. The resultant solid was re-suspended in dichloromethane, filtered, and dried in vacuo to provide 13 mg (90%) of the title compound as a solid.1H NMR-(DMSO-d6)δ 9.15 (s, 1H), 8.09-8.01 (m, 3H), 7.93 (s, 1H), 7.68-7.57 (m, 3H), 7.45 (d, 2H, J=7.8 Hz), 6.99 (d, 2H, J=8.1 Hz), 4.18-4.12 (m, 2H), 3.90-3.75 (m, 7H), 3.56-3.42 (m, 3H), 3.19-3.13 (m, 2H), 2.88-2.82 (m, 2H);LC-MS: m/z: 574.7 [M+H]+, Rf=1.36 min.
	With [bis(acetoxy)iodo]benzene In dichloromethane	2; 3 Commercially available 2-naphthylacetic acid (3 g, 16.1 mmol) m 8 mL of anhydrous diethyl ether was added dropwise to a solution of lithium aluminum hydride (1.2 g, 32.2 mmol) in 8 mL of anhydrous diethyl ether under nitrogen atmosphere. The reaction mixture was aged for 2 h, quenched with aqueous Rochelle salt, stirred for an additional 2 h, partitioned between saturated aqueous NaHCO3 and diethyl ether, the organic phase was separated and dried over anhydrous sodium sulfate, and then evaporated under reduced pressure to provide the crude alcohol product (1.4 g). This alcohol (1.0 g, 5.81 mmol) was oxidized directly with iodobenzene diacetate (2.1 g, 6.5 mmol) and catalytic TEMPO (10%) in methylene chloride solvent (20 mL). The reaction mixture was quenched with aqueous sodium thiosulfate, partitioned with methylene chloride, the organic phase washed with aqueous NaHCO3, and the organic phase concentrated in vacuo to provide the clean aldehyde product. This crude aldehyde intermediate (500 mg, 2.9 mmol) was combined with methyl (triphenylphosphoranyhdene) acetate (1.47 g, 4.4 mmol) in toluene (10 mL), and the reaction mixture heated at reflux for 4 h. The mixture was concentrated in vacuo to a residue which was purified by flash column chromatography (S1O2, EtOAc/hexanes) to give the desired methyl enoate. This intermediate was then dissolved in tetrahydrofuran (10 mL), treated with aqueous 1N NaOH (5 mL), refluxed for 2 h, the mixture cooled, acidified and extracted with ethyl acetate. The organic phase was concentrated in vacuo to provide the enoic acid, which was treated with catalytic palladium on carbon in methanol (20 mL), and hydrogenated at 1 atmosphere with a hydrogen-filled balloon for 12 h. The reaction mixture was filtered over celite and concentrated in vacuo to provide the clean crude acid defined as Compound A in Scheme 2. Compound A (50 mg, 0.234 mmol) was converted into EXAMPLE 3 in a similar manner as m EXAMPLE 1 and illustrated in Scheme 1 using anthranihc acid directly in the amide coupling reaction The product Was purified via preparative RPHPLC and then recrystallization (diethyl ether/hexane) to give the desired product. 1H NMR (CDCl3, 500 MHz) δ 10.93 (s, 1H), 8 79 (d, 1H), 8.11 (d, 1H), 7.80(m, 3H), 7.68(s, 1H), 7.61(t, 1H), 7.40(m, 2H), 7.38 (d, 1H), 7.12 (t, 1H), 2.92 (t, 2H), 2.53 (t, 2H), 2.22 (m, 2H); LCMS m/z 332 (M+-1).
	With sulfur trioxide pyridine complex; triethylamine In dichloromethane; dimethyl sulfoxide at 20℃; for 1h;
	With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetonitrile at 80℃; Inert atmosphere;
	Stage #1: naphthalen-2-ethanol With trichloroisocyanuric acid In dichloromethane at 0℃; for 0.0833333h; Stage #2: With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In dichloromethane at 20℃; for 0.166667h;
	With Dess-Martin periodane In dichloromethane at 20℃; for 1.5h; Inert atmosphere;

Reference： [1]Ellingboe, John W.; Lombardo, Louis J.; Alessi, Thomas R.; Nguyen, Thomas T.; Guzzo, Frieda; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 17, p. 2485 - 2493]
[2]Zhang, Xiaoxia; Sarkar, Sampa; Larock, Richard C. [Journal of Organic Chemistry, 2006, vol. 71, # 1, p. 236 - 243]
[3]Location in patent: experimental part Revelant, Germain; Dunand, Sandrine; Hesse, Stephanie; Kirsch, Gilbert [Synthesis, 2011, # 18, p. 2935 - 2940]
[4]Roda, Gabriella; Riva, Sergio; Danieli, Bruno [Tetrahedron Asymmetry, 1999, vol. 10, # 20, p. 3939 - 3949]
[5]Moreno-Cinos, Carlos; Sassetti, Elisa; Salado, Irene G.; Witt, Gesa; Benramdane, Siham; Reinhardt, Laura; Cruz, Cristina D.; Joossens, Jurgen; Van Der Veken, Pieter; Brötz-Oesterhelt, Heike; Tammela, Päivi; Winterhalter, Mathias; Gribbon, Philip; Windshügel, Björn; Augustyns, Koen [Journal of Medicinal Chemistry, 2019, vol. 62, # 2, p. 774 - 797]
[6]Matsuo, Jun-Ichi; Kitagawa, Hideo; Iida, Daisuke; Mukaiyama, Teruaki [Chemistry Letters, 2001, # 2, p. 150 - 151]
[7]Matsuo, Jun-Ichi; Iida, Daisuke; Tatani, Kazuya; Mukaiyama, Teruaki [Bulletin of the Chemical Society of Japan, 2002, vol. 75, # 2, p. 223 - 234]
[8]Current Patent Assignee: MEIJI HOLDINGS CO., LTD - EP1661904, 2006, A1 Location in patent: Page/Page column 48
[9]Current Patent Assignee: NOVO NORDISK A/S; ONTOGEN CORP - EP1214324, 2006, B1 Location in patent: Page/Page column 49-50
[10]Current Patent Assignee: ONTOGEN CORP; NOVO NORDISK A/S - US7115624, 2006, B1 Location in patent: Page/Page column 150-151
[11]Current Patent Assignee: MERCK & CO INC - WO2006/52555, 2006, A2 Location in patent: Page/Page column 26; 40-41
[12]Gising, Johan; Belfrage, Anna Karin; Alogheli, Hiba; Ehrenberg, Angelica; Åkerblom, Eva; Svensson, Richard; Artursson, Per; Karlén, Anders; Danielson, U. Helena; Larhed, Mats; Sandström, Anja [Journal of Medicinal Chemistry, 2014, vol. 57, # 5, p. 1790 - 1801]
[13]Kondoh, Azusa; Odaira, Kenta; Terada, Masahiro [Angewandte Chemie - International Edition, 2015, vol. 54, # 38, p. 11240 - 11244][Angew. Chem., 2015, vol. 127, p. 11392 - 11396]
[14]Wang, Yujie; Shao, Zhihui; Zhang, Kun; Liu, Qiang [Angewandte Chemie - International Edition, 2018, vol. 57, # 46, p. 15143 - 15147][Angew. Chem., 2018, vol. 130, p. 15363 - 15367,5]
[15]Havare, Nizam; Plattner, Dietmar A. [Organic Letters, 2012, vol. 14, # 19, p. 5078 - 5081,4]

8
[ 1485-07-0 ]
[ 20849-71-2 ]

Yield	Reaction Conditions	Operation in experiment
83.9%	With pyridine; thionyl chloride In diethyl ether Heating;
	With methanesulfonyl chloride; triethylamine In dichloromethane at 0 - 20℃; for 12.08h; Inert atmosphere;	12.2 Step 2: Preparation of 2-(2-chloroethyl)naphthalene MsCl (238 mg, 2.08 mmol) was added dropwise into a mixture of 2-(naphthalen-2- yl)ethan-l-ol (300 mg, 1.74 mmol), dichloromethane (10 mL), and TEA (527 mg, 5.21 mmol) at 0°C in 5 min under nitrogen. The resulting solution was stirred for 12h at room temperature. The resulting mixture was concentrated under vacuum. This resulted in the title compound (400 mg, crude) as a white solid, which was used for the next step without any further purification.

Reference： [1]Olah,G.A.; Singh,B.P. [Journal of the American Chemical Society, 1982, vol. 104, p. 5168]
[2]Current Patent Assignee: ROCHE HOLDING AG; PARAZA PHARMA INC - WO2018/96159, 2018, A1 Location in patent: Paragraph 0261; 0262; 0265; 0266

9
[ 1485-07-0 ]
[ 75325-83-6 ]

Yield	Reaction Conditions	Operation in experiment
79%	With diphosphorus tetraiodide In carbon disulfide for 48h; Ambient temperature;
63%	With 1H-imidazole; iodine; triphenylphosphine In dichloromethane Cooling with ice;
57%	With 1H-imidazole; iodine In dichloromethane at 0 - 20℃; for 16h;

	With 1H-imidazole; triphenylphosphine diiodide In dichloromethane Ambient temperature;
	Multi-step reaction with 2 steps 1: 90 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C 2: 88 percent / NaI / acetonitrile / 36 h
2 g	With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 0 - 20℃; for 1.16667h; Inert atmosphere;	2-(2-Iodoethyl)naphthalene (4n) 2-Naphthylacetic acid (2.5 g, 13 mmol) in Et2O (56 mL) was added slowly to LAH (1.0 g, 27 mmol) in Et2O (11 ml) and the mixture was stirred for 15 min at r.t. The crude reaction mixture was quenched by adding H2O (1 mL), 15% aq NaOH (1 mL), and H2O (3 mL) sequentially. The resulting white solid was removed by filtering through a Celite pad (EtOAc). The organic layer was separated and dried over Na2SO4. After removal of the solvent, the crude product was purified by Yamazen YFLC AI-580 using Universal Column SiOH (hexane/EtOAc) to afford crude 2-(2-naphthyl)ethan-1-ol (2.1 g) as a white solid. According to general procedure A, the crude alcohol (2.1 g, ca. 12 mmol) was treated with iodine (3.4 g, 13 mmol), PPh3 (3.5 g, 13 mmol), and imidazole (990 mg, 15 mmol). The crude product was purified by Yamazen YFLC AI-580 using Universal Column SiOH (hexane/EtOAc) to provide 4n. Yield: 2.0 g, 6.9 mmol (52% over 2 steps); white solid; mp 71-72 °C; Rf = 0.50 (hexane/EtOAc 9:1, UV). NMR spectra of the obtained product were consistent with the reported data.31 1H NMR (400 MHz, CDCl3): δ = 7.83-7.78 (m, 3 H), 7.65 (s, 1 H), 7.49-7.44 (m, 2 H), 7.32 (dd, J = 8.3, 1.6 Hz, 1 H), 3.44 (t, J = 7.4 Hz, 2 H), 3.34 (t, J = 7.4 Hz, 2 H). 13C NMR (100 MHz, CDCl3): δ = 138.0, 133.5, 132.3, 128.3, 127.7, 127.6, 126.9, 126.5, 126.2, 125.6, 40.4, 5.4.

Reference： [1]Pataki; Harvey [Journal of Organic Chemistry, 1982, vol. 47, # 1, p. 20 - 22]
[2]Liu, Bingxue; Liu, Qiang; Liu, Xufang [Angewandte Chemie - International Edition, 2020, vol. 59, # 17, p. 6750 - 6755][Angew. Chem., 2020, vol. 132, # 17, p. 6816 - 6821,6]
[3]Boehm, Philip; Cacherat, Bastien; Lee, Yong Ho; Martini, Tristano; Morandi, Bill [Angewandte Chemie - International Edition, 2021, vol. 60, # 31, p. 17211 - 17217][Angew. Chem., 2021, vol. 133, # 31, p. 17348 - 17355]
[4]Ornstein, Paul L.; Bleisch, Thomas J.; Arnold, M. Brian; Wright, Rebecca A.; Johnson, Bryan G.; Schoepp, Darryle D. [Journal of Medicinal Chemistry, 1998, vol. 41, # 3, p. 346 - 357]
[5]Newcomb, Lisa F.; Haque, Tasir S.; Gellman, Samuel H. [Journal of the American Chemical Society, 1995, vol. 117, # 24, p. 6509 - 6519]
[6]Kojima, Masahiro; Matsunaga, Shigeki [Synthesis, 2020, vol. 52, # 13, p. 1934 - 1946]

10
[ 2876-71-3 ]
[ 1485-07-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With lithium aluminium tetrahydride In diethyl ether at 0℃; for 2h;
	With diisobutylaluminium hydride In tetrahydrofuran; toluene at 20℃;
	With hydrogenchloride; diisobutylaluminium hydride In tetrahydrofuran; hexane; water at 0 - 20℃; Inert atmosphere;

Reference： [1]Novak, Lajos; Rohaly, Janos; Poppe, Laszlo; Hornyanszky, Gabor; Kolonits, Pal; et al. [Liebigs Annalen der Chemie, 1992, # 2, p. 145 - 158]
[2]Location in patent: experimental part Revelant, Germain; Dunand, Sandrine; Hesse, Stephanie; Kirsch, Gilbert [Synthesis, 2011, # 18, p. 2935 - 2940]
[3]Kondoh, Azusa; Odaira, Kenta; Terada, Masahiro [Angewandte Chemie - International Edition, 2015, vol. 54, # 38, p. 11240 - 11244][Angew. Chem., 2015, vol. 127, p. 11392 - 11396]

11
2-(2-Naphthalen-2-yl-ethoxy)-tetrahydro-pyran [ No CAS ]
[ 1485-07-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	In methanol for 2h;

Reference： [1]Olah, George A.; Husain, Altaf; Singh, Brij P. [Synthesis, 1983, # 11, p. 892 - 895]

12
[ 1485-07-0 ]
[ 124-63-0 ]
[ 102072-41-3 ]

Yield	Reaction Conditions	Operation in experiment
95.2%	With triethylamine In tetrahydrofuran for 3h; Ambient temperature;
90%	With triethylamine In dichloromethane at 0℃; for 2h;
	With triethylamine In dichloromethane at 0℃; for 1h; Heating;

	With triethylamine In tetrahydrofuran at 22℃; for 3h;
	In dichloromethane at 0 - 20℃;
	With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 2.5h;	4 A solution, cooled to 0° C., of 0.13 g (0.75 mmol) of 2-naphthalen-2-ylethanol and 0.19 ml (1.13 mmol) of diisopropylethylamine in 7.5 ml of dichloromethane is admixed with 0.07 ml (0.9 mmol) of methanesulphonyl chloride. Stirring is continued in the cold for 0.5 hour, then at ambient temperature for 2 hours. The solution is concentrated under reduced pressure. The residue is taken up in 5 ml of acetonitrile, and 0.12 g (0.5 mmol) of 2-(methylamino)-2-oxoethyl piperazine-1-carboxylate hydrochloride, prepared in accordance with Example 3.3., and 0.20 g (1.5 mmol) of potassium carbonate are added. The mixture is heated at 70° C. for 16 hours. After cooling to ambient temperature, it is concentrated under reduced pressure. The residue is suspended in dichloromethane and washed with saturated sodium bicarbonate solution and then with water. The organic phase is recovered by filtration on a hydrophobic membrane and is concentrated under reduced pressure. Chromatography on silica gel, eluting with a 95/5 mixture of dichloromethane and methanol, followed by crystallization from diisopropyl ether, give 0.069 g of product in the form of a white solid. LC-MS: M+H=356 Melting point: 133-135° C. 1H NMR (CDCl3) δ(ppm): 7.85 (m, 3H); 7.65 (s, 1H); 7.55-7.30(m, 3H); 6.05 (broad s, 1H); 4.60 (s, 2H); 3.55 (m, 4H); 3.05-2.65 (m, 7H); 2.55 (m, 4H).
	With triethylamine In dichloromethane at 0 - 20℃; for 3h;

Reference： [1]Robertson; Krushinski; Beedle; Leander; Wong; Rathbun [Journal of Medicinal Chemistry, 1986, vol. 29, # 9, p. 1577 - 1586]
[2]Newcomb, Lisa F.; Haque, Tasir S.; Gellman, Samuel H. [Journal of the American Chemical Society, 1995, vol. 117, # 24, p. 6509 - 6519]
[3]Hardy, George W.; Lowe, Lawrence A.; Mills, Gail; Sang, Pang Yih; Simpkin, Dean S. A.; et al. [Journal of Medicinal Chemistry, 1989, vol. 32, # 5, p. 1108 - 1118]
[4]Nugent, Richard A.; Schlachter, Stephen T.; Murphy, Michael J.; Cleek, Gary J.; Poel, Toni J.; Wishka, Donn G.; Graber, David R.; Yagi, Yoshihiko; Keiser, Barbara J.; Olmsted, Robert A.; Kopta, Laurie A.; Swaney, Steven M.; Poppe, Susan M.; Morris, Joel; Tarpley, W. Gary; Thomas, Richard C. [Journal of Medicinal Chemistry, 1998, vol. 41, # 20, p. 3793 - 3803]
[5]Nersesian, Diana L.; Black, Lawrence A.; Miller, Thomas R.; Vortherms, Timothy A.; Esbenshade, Timothy A.; Hancock, Arthur A.; Cowart, Marlon D. [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 1, p. 355 - 359]
[6]Current Patent Assignee: SANOFI - US2007/27141, 2007, A1 Location in patent: Page/Page column 7
[7]Suzuki, Takayoshi; Ota, Yosuke; Ri, Masaki; Bando, Masashige; Gotoh, Aogu; Itoh, Yukihiro; Tsumoto, Hiroki; Tatum, Prima R.; Mizukami, Tamio; Nakagawa, Hidehiko; Iida, Shinsuke; Ueda, Ryuzo; Shirahige, Katsuhiko; Miyata, Naoki [Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9562 - 9575]

13
[ 89113-45-1 ]
[ 1485-07-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	With aluminium trichloride; sodium iodide In acetonitrile for 8h; Ambient temperature;

Reference： [1]Node, Manabu; Ohta, Keiichiro; Kajimoto, Tetsuya; Nishide, Kiyoharu; Fujita, Eiichi; Fuji, Kaoru [Chemical and pharmaceutical bulletin, 1983, vol. 31, # 11, p. 4178 - 4180]

14
[ 1485-07-0 ]
[ 75-36-5 ]
[ 83053-19-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	With triethylamine In dichloromethane at 0 - 20℃;

Reference： [1]Houck, Hannes A.; Blasco, Eva; Du Prez, Filip E.; Barner-Kowollik, Christopher [Journal of the American Chemical Society, 2019, vol. 141, # 31, p. 12329 - 12337]
[2]Gilbert, Andrew; Heath, Peter; Kashoulis-Koupparis, Annoula; Ellis-Davies, Graham C. R.; Firth, Susan M. [Journal of the Chemical Society. Perkin transactions I, 1988, p. 31 - 36]

15
[ 1485-07-0 ]
[ 5906-99-0 ]
[ 939-27-5 ]

Reference： [1]Tetrahedron Letters,1997,vol. 38,p. 6569 - 6572

16
[ 1485-07-0 ]
[ 5906-99-0 ]
C₁₈H₁₇N₃O₄S [ No CAS ]

Reference： [1]Tetrahedron Letters,1997,vol. 38,p. 6569 - 6572

17
[ 827-54-3 ]
[ 1485-07-0 ]
[ 27544-18-9 ]
[ 52193-85-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-naphthylethylene With benzo[1,3,2]dioxaborole In toluene at 20℃; for 2h; Stage #2: With sodium hydroxide; water; dihydrogen peroxide In toluene at 20℃; for 2h; Title compound not separated from byproducts;
	Stage #1: 2-naphthylethylene With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; (1R,2R)-1,2-bis(dicyclohexylphosphanyl)cyclohexane; benzo[1,3,2]dioxaborole In 1,2-dimethoxyethane at -35℃; for 17h; Stage #2: With potassium hydroxide; dihydrogen peroxide In 1,2-dimethoxyethane Title compound not separated from byproducts;
	Stage #1: 2-naphthylethylene With diethoxymethylane In toluene at 30℃; for 72h; Stage #2: With potassium fluoride; dihydrogen peroxide; potassium carbonate In tetrahydrofuran; methanol at 0℃;

Reference： [1]Doucet, Henri; Fernandez, Elena; Layzell, Timothy P.; Brown, John M. [Chemistry - A European Journal, 1999, vol. 5, # 4, p. 1320 - 1330]
[2]Demay, Steandphane; Volant, Florence; Knochel, Paul [Angewandte Chemie - International Edition, 2001, vol. 40, # 7, p. 1235 - 1238]
[3]Tsuchiya, Yasunori; Uchimura, Hirofumi; Kobayashi, Kazuki; Nishiyama, Hisao [Synlett, 2004, # 12, p. 2099 - 2102]

18
benzylsulfanyl-naphthalen-2-yl-acetaldehyde [ No CAS ]
[ 1485-07-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	With 2,2'-azobis(isobutyronitrile); n-Bu₃SH In benzene Heating;

Reference： [1]Satoh, Tsuyoshi; Kubota, Ko-Ichi [Tetrahedron Letters, 2000, vol. 41, # 13, p. 2121 - 2124]

19
[ 374928-98-0 ]
[ 1485-07-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	With fluorosilicic acid In methanol; acetonitrile for 72h;

Reference： [1]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]

20
[ 374928-95-7 ]
[ 1485-07-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With fluorosilicic acid In methanol; acetonitrile for 36h;
	Multi-step reaction with 5 steps 1.1: 90 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 36 h 2.1: Br₂ / diethyl ether / 0.5 h / 0 °C 2.2: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C 3.1: 99 percent / H₂SiF₆ / acetonitrile; various solvent(s) / 24 h 4.1: Br₂ / diethyl ether / 0 °C 4.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 5.1: 100 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 144 h
	Multi-step reaction with 3 steps 1.1: 90 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 36 h 2.1: Br₂ / diethyl ether / 0.5 h / 0 °C 2.2: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C 3.1: 99 percent / H₂SiF₆ / acetonitrile; various solvent(s) / 24 h

	Multi-step reaction with 5 steps 1.1: 90 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 36 h 2.1: Br₂ / diethyl ether / 0 °C 2.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 3.1: 100 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 144 h 4.1: Br₂ / diethyl ether / 0.5 h / 0 °C 4.2: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C 5.1: 99 percent / H₂SiF₆ / acetonitrile; various solvent(s) / 24 h
	Multi-step reaction with 3 steps 1.1: 90 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 36 h 2.1: Br₂ / diethyl ether / 0 °C 2.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 3.1: 100 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 144 h

Reference： [1]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[2]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[3]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[4]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[5]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]

21
[ 374928-84-4 ]
[ 1485-07-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With fluorosilicic acid In acetonitrile for 24h;
	Multi-step reaction with 5 steps 1.1: 99 percent / H₂SiF₆ / acetonitrile; various solvent(s) / 24 h 2.1: Br₂ / diethyl ether / 0 °C 2.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 3.1: 90 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 36 h 4.1: Br₂ / diethyl ether / 0 °C 4.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 5.1: 100 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 144 h
	Multi-step reaction with 3 steps 1.1: 99 percent / H₂SiF₆ / acetonitrile; various solvent(s) / 24 h 2.1: Br₂ / diethyl ether / 0 °C 2.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 3.1: 90 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 36 h

	Multi-step reaction with 5 steps 1.1: 99 percent / H₂SiF₆ / acetonitrile; various solvent(s) / 24 h 2.1: Br₂ / diethyl ether / 0 °C 2.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 3.1: 100 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 144 h 4.1: Br₂ / diethyl ether / 0 °C 4.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 5.1: 90 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 36 h
	Multi-step reaction with 3 steps 1.1: 99 percent / H₂SiF₆ / acetonitrile; various solvent(s) / 24 h 2.1: Br₂ / diethyl ether / 0 °C 2.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 3.1: 100 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 144 h

Reference： [1]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[2]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[3]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[4]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[5]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]

22
[ 374928-94-6 ]
[ 1485-07-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With fluorosilicic acid In methanol; acetonitrile for 144h;
	Multi-step reaction with 5 steps 1.1: 100 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 144 h 2.1: Br₂ / diethyl ether / 0 °C 2.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 3.1: 90 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 36 h 4.1: Br₂ / diethyl ether / 0.5 h / 0 °C 4.2: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C 5.1: 99 percent / H₂SiF₆ / acetonitrile; various solvent(s) / 24 h
	Multi-step reaction with 3 steps 1.1: 100 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 144 h 2.1: Br₂ / diethyl ether / 0 °C 2.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 3.1: 90 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 36 h

	Multi-step reaction with 5 steps 1.1: 100 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 144 h 2.1: Br₂ / diethyl ether / 0.5 h / 0 °C 2.2: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C 3.1: 99 percent / H₂SiF₆ / acetonitrile; various solvent(s) / 24 h 4.1: Br₂ / diethyl ether / 0 °C 4.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 5.1: 90 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 36 h
	Multi-step reaction with 3 steps 1.1: 100 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 144 h 2.1: Br₂ / diethyl ether / 0.5 h / 0 °C 2.2: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C 3.1: 99 percent / H₂SiF₆ / acetonitrile; various solvent(s) / 24 h

Reference： [1]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[2]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[3]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[4]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[5]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]

23
[ 102072-41-3 ]
[ 1485-07-0 ]
[ 827-54-3 ]
[ 463934-12-5 ]

Yield	Reaction Conditions	Operation in experiment
1: 73% 2: 9% 3: 10%	With potassium fluoride; water; 1-butyl-3-methylimidazolium Tetrafluoroborate In acetonitrile at 100℃; for 2h;

Reference： [1]Kim, Dong Wook; Song, Choong Eui; Chi, Dae Yoon [Journal of the American Chemical Society, 2002, vol. 124, # 35, p. 10278 - 10279]

24
[ 109-09-1 ]
[ 201230-82-2 ]
[ 1485-07-0 ]
pyridine-2-carboxylic acid 2-naphthalen-2-yl-ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis(benzonitrile)palladium(II) dichloride; 1,3-bis-(diphenylphosphino)propane; triethylamine In N,N-dimethyl-formamide at 130℃; for 14h;

Reference： [1]Blaser, Hans-Ulrich; Diggelmann, Martin; Meier, Hans; Naud, Frederic; Scheppach, Elke; Schnyder, Anita; Studer, Martin [Journal of Organic Chemistry, 2003, vol. 68, # 9, p. 3725 - 3728]

25
[ 1485-07-0 ]
[ 2017-68-7 ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 7745 - 7746
[2]Tetrahedron Letters,2003,vol. 44,p. 4153 - 4156

26
[ 2086-62-6 ]
[ 1485-07-0 ]

Yield	Reaction Conditions	Operation in experiment
80%	With water In 1,4-dioxane at 110℃; for 72h;

Reference： [1]Kim, Dong Wook; Hong, Dong Jin; Seo, Jai Woong; Kim, Hoon Sik; Kim, Hong Kon; Song, Choong Eui; Chi, Dae Yoon [Journal of Organic Chemistry, 2004, vol. 69, # 9, p. 3186 - 3189]

27
[ 1485-07-0 ]
[ 406953-48-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	With nicotinoyl azide; triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 3h;
	Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 3 h / 0 - 20 °C 2: sodium azide / dimethylsulfoxide-d6 / 2 h / 80 °C
	Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 3 h / 20 °C / Cooling with ice 2: sodium azide / dimethyl sulfoxide / 2 h / 80 °C

Reference： [1]Papeo, Gianluca; Posteri, Helena; Vianello, Paola; Varasi, Mario [Synthesis, 2004, # 17, p. 2886 - 2892]
[2]Suzuki, Takayoshi; Ota, Yosuke; Ri, Masaki; Bando, Masashige; Gotoh, Aogu; Itoh, Yukihiro; Tsumoto, Hiroki; Tatum, Prima R.; Mizukami, Tamio; Nakagawa, Hidehiko; Iida, Shinsuke; Ueda, Ryuzo; Shirahige, Katsuhiko; Miyata, Naoki [Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9562 - 9575]
[3]Current Patent Assignee: NAGOYA CITY UNIVERSITY - JP5725475, 2015, B2

28
[ 170219-37-1 ]
[ 1485-07-0 ]
[ 850249-50-2 ]

Yield	Reaction Conditions	Operation in experiment
181.9 mg	Stage #1: 3,4-di-O-benzyl-6-O-(5'-azidopentyl)-β-D-glucal In dichloromethane Stage #2: naphthalen-2-ethanol With zinc(II) chloride In tetrahydrofuran; diethyl ether at -78 - 20℃; for 48h;

Reference： [1]Angeles, Angie R.; Neagu, Irina; Birzin, Elizabeth T.; Thornton, Edward R.; Smith III, Amos B.; Hirschmann, Ralph [Organic Letters, 2005, vol. 7, # 6, p. 1121 - 1124]

29
[ 914300-10-0 ]
[ 1485-07-0 ]

Yield	Reaction Conditions	Operation in experiment
57%	With 4,4'-di-tert-butylbiphenyl; lithium In tetrahydrofuran at -40℃; for 1h;

Reference： [1]Gómez, Cecilia; Maciá, Beatriz; Lillo, Victor J.; Yus, Miguel [Tetrahedron, 2006, vol. 62, # 42, p. 9832 - 9839]

30
[ 1485-07-0 ]
[ 356056-14-9 ]
[ 374928-95-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: diisopropyl-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane With bromine In diethyl ether at 0℃; Stage #2: naphthalen-2-ethanol With dmap; triethylamine In dichloromethane at 0℃; Further stages.;

Reference： [1]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]

31
[ 1485-07-0 ]
[ 356056-15-0 ]
[ 374928-84-4 ]

Yield	Reaction Conditions	Operation in experiment
2.0 g	Stage #1: diisopropyl(3’,3’,4’,4’,5’,5’,6’,6’,7’,7’,8’,8’,9’,9’,10’,10’-heptadecafluorodecyl)silane With bromine In diethyl ether at 0℃; for 0.5h; Stage #2: naphthalen-2-ethanol With dmap; triethylamine In dichloromethane at 0℃; for 1.5h; Further stages.;

Reference： [1]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]

32
[ 1485-07-0 ]
[ 356056-13-8 ]
[ 374928-98-0 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: diisopropyl(3,3,4,4,5,5,6,6,6-nonafluorohexyl)silane With bromine In diethyl ether at 0℃; Stage #2: naphthalen-2-ethanol With dmap; triethylamine In dichloromethane at 0℃; Further stages.;

Reference： [1]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]

33
[ 1485-07-0 ]
[ 356056-16-1 ]
[ 374928-94-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: diisopropyl-(1H,1H,2H,2H-perfluorododecyl)silane With bromine In diethyl ether at 0℃; Stage #2: naphthalen-2-ethanol With dmap; triethylamine In dichloromethane at 0℃; Further stages.;

Reference： [1]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]

34
[ 1485-07-0 ]
[ 62-53-3 ]
[ 108079-37-4 ]

Yield	Reaction Conditions	Operation in experiment
89%	With 1,1'-bis(diphenylphosphino)ferrocene; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ In toluene at 20℃; for 24.1667h; Inert atmosphere; Reflux;
	With 3 A molecular sieve; potassium carbonate In toluene for 24h; Heating;

Reference： [1]Hamid, M. Haniti S. A.; Allen, C. Liana; Lamb, Gareth W.; Maxwell, Aoife C.; Maytum, Hannah C.; et al. [Journal of the American Chemical Society, 2009, vol. 131, p. 1766 - 1774]
[2]Hamid, Malai Haniti S. A.; Williams, Jonathan M. J. [Chemical Communications, 2007, # 7, p. 725 - 727]

35
[ 1485-07-0 ]
[ 2873-29-2 ]
2-naphthalenoethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With niobium pentachloride In dichloromethane at 20℃; for 0.5h;

Reference： [1]de Oliveira, Ronaldo N.; de Melo, Adriana C.N.; Srivastava, Rajendra M.; Sinou, Denis [Heterocycles, 2006, vol. 68, # 12, p. 2607 - 2613]

36
[ 1485-07-0 ]
[ 374928-98-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: Br₂ / diethyl ether / 0 °C 1.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 2.1: 90 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 36 h 3.1: Br₂ / diethyl ether / 0.5 h / 0 °C 3.2: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C 4.1: 99 percent / H₂SiF₆ / acetonitrile; various solvent(s) / 24 h 5.1: Br₂ / diethyl ether / 0 °C 5.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C
	Multi-step reaction with 7 steps 1.1: Br₂ / diethyl ether / 0 °C 1.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 2.1: 90 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 36 h 3.1: Br₂ / diethyl ether / 0.5 h / 0 °C 3.2: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C 4.1: 99 percent / H₂SiF₆ / acetonitrile; various solvent(s) / 24 h 5.1: Br₂ / diethyl ether / 0 °C 5.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 6.1: 100 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 144 h 7.1: Br₂ / diethyl ether / 0 °C 7.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C
	Multi-step reaction with 3 steps 1.1: Br₂ / diethyl ether / 0 °C 1.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 2.1: 90 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 36 h 3.1: Br₂ / diethyl ether / 0 °C 3.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C

	Multi-step reaction with 7 steps 1.1: Br₂ / diethyl ether / 0 °C 1.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 2.1: 90 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 36 h 3.1: Br₂ / diethyl ether / 0 °C 3.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 4.1: 100 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 144 h 5.1: Br₂ / diethyl ether / 0.5 h / 0 °C 5.2: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C 6.1: 99 percent / H₂SiF₆ / acetonitrile; various solvent(s) / 24 h 7.1: Br₂ / diethyl ether / 0 °C 7.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C
	Multi-step reaction with 5 steps 1.1: Br₂ / diethyl ether / 0 °C 1.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 2.1: 90 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 36 h 3.1: Br₂ / diethyl ether / 0 °C 3.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 4.1: 100 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 144 h 5.1: Br₂ / diethyl ether / 0 °C 5.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C
	Multi-step reaction with 5 steps 1.1: Br₂ / diethyl ether / 0.5 h / 0 °C 1.2: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C 2.1: 99 percent / H₂SiF₆ / acetonitrile; various solvent(s) / 24 h 3.1: Br₂ / diethyl ether / 0 °C 3.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 4.1: 90 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 36 h 5.1: Br₂ / diethyl ether / 0 °C 5.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C
	Multi-step reaction with 7 steps 1.1: Br₂ / diethyl ether / 0.5 h / 0 °C 1.2: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C 2.1: 99 percent / H₂SiF₆ / acetonitrile; various solvent(s) / 24 h 3.1: Br₂ / diethyl ether / 0 °C 3.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 4.1: 90 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 36 h 5.1: Br₂ / diethyl ether / 0 °C 5.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 6.1: 100 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 144 h 7.1: Br₂ / diethyl ether / 0 °C 7.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C
	Multi-step reaction with 3 steps 1.1: Br₂ / diethyl ether / 0.5 h / 0 °C 1.2: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C 2.1: 99 percent / H₂SiF₆ / acetonitrile; various solvent(s) / 24 h 3.1: Br₂ / diethyl ether / 0 °C 3.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C
	Multi-step reaction with 7 steps 1.1: Br₂ / diethyl ether / 0.5 h / 0 °C 1.2: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C 2.1: 99 percent / H₂SiF₆ / acetonitrile; various solvent(s) / 24 h 3.1: Br₂ / diethyl ether / 0 °C 3.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 4.1: 100 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 144 h 5.1: Br₂ / diethyl ether / 0 °C 5.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 6.1: 90 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 36 h 7.1: Br₂ / diethyl ether / 0 °C 7.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C
	Multi-step reaction with 5 steps 1.1: Br₂ / diethyl ether / 0.5 h / 0 °C 1.2: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C 2.1: 99 percent / H₂SiF₆ / acetonitrile; various solvent(s) / 24 h 3.1: Br₂ / diethyl ether / 0 °C 3.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 4.1: 100 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 144 h 5.1: Br₂ / diethyl ether / 0 °C 5.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C
	Multi-step reaction with 7 steps 1.1: Br₂ / diethyl ether / 0 °C 1.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 2.1: 100 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 144 h 3.1: Br₂ / diethyl ether / 0 °C 3.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 4.1: 90 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 36 h 5.1: Br₂ / diethyl ether / 0.5 h / 0 °C 5.2: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C 6.1: 99 percent / H₂SiF₆ / acetonitrile; various solvent(s) / 24 h 7.1: Br₂ / diethyl ether / 0 °C 7.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C
	Multi-step reaction with 5 steps 1.1: Br₂ / diethyl ether / 0 °C 1.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 2.1: 100 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 144 h 3.1: Br₂ / diethyl ether / 0 °C 3.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 4.1: 90 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 36 h 5.1: Br₂ / diethyl ether / 0 °C 5.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C
	Multi-step reaction with 7 steps 1.1: Br₂ / diethyl ether / 0 °C 1.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 2.1: 100 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 144 h 3.1: Br₂ / diethyl ether / 0.5 h / 0 °C 3.2: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C 4.1: 99 percent / H₂SiF₆ / acetonitrile; various solvent(s) / 24 h 5.1: Br₂ / diethyl ether / 0 °C 5.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 6.1: 90 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 36 h 7.1: Br₂ / diethyl ether / 0 °C 7.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C
	Multi-step reaction with 5 steps 1.1: Br₂ / diethyl ether / 0 °C 1.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 2.1: 100 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 144 h 3.1: Br₂ / diethyl ether / 0.5 h / 0 °C 3.2: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C 4.1: 99 percent / H₂SiF₆ / acetonitrile; various solvent(s) / 24 h 5.1: Br₂ / diethyl ether / 0 °C 5.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C
	Multi-step reaction with 3 steps 1.1: Br₂ / diethyl ether / 0 °C 1.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 2.1: 100 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 144 h 3.1: Br₂ / diethyl ether / 0 °C 3.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C

Reference： [1]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[2]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[3]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[4]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[5]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[6]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[7]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[8]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[9]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[10]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[11]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[12]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[13]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[14]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[15]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]

37
[ 1485-07-0 ]
[ 374928-95-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: Br₂ / diethyl ether / 0.5 h / 0 °C 1.2: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C 2.1: 99 percent / H₂SiF₆ / acetonitrile; various solvent(s) / 24 h 3.1: Br₂ / diethyl ether / 0 °C 3.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C
	Multi-step reaction with 5 steps 1.1: Br₂ / diethyl ether / 0.5 h / 0 °C 1.2: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C 2.1: 99 percent / H₂SiF₆ / acetonitrile; various solvent(s) / 24 h 3.1: Br₂ / diethyl ether / 0 °C 3.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 4.1: 100 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 144 h 5.1: Br₂ / diethyl ether / 0 °C 5.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C
	Multi-step reaction with 3 steps 1.1: Br₂ / diethyl ether / 0 °C 1.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 2.1: 100 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 144 h 3.1: Br₂ / diethyl ether / 0 °C 3.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C

Multi-step reaction with 5 steps 1.1: Br₂ / diethyl ether / 0 °C 1.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 2.1: 100 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 144 h 3.1: Br₂ / diethyl ether / 0.5 h / 0 °C 3.2: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C 4.1: 99 percent / H₂SiF₆ / acetonitrile; various solvent(s) / 24 h 5.1: Br₂ / diethyl ether / 0 °C 5.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C

Reference： [1]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[2]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[3]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[4]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]

38
[ 1485-07-0 ]
[ 374928-84-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: Br₂ / diethyl ether / 0 °C 1.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 2.1: 90 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 36 h 3.1: Br₂ / diethyl ether / 0.5 h / 0 °C 3.2: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C
	Multi-step reaction with 5 steps 1.1: Br₂ / diethyl ether / 0 °C 1.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 2.1: 90 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 36 h 3.1: Br₂ / diethyl ether / 0 °C 3.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 4.1: 100 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 144 h 5.1: Br₂ / diethyl ether / 0.5 h / 0 °C 5.2: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C
	Multi-step reaction with 5 steps 1.1: Br₂ / diethyl ether / 0 °C 1.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 2.1: 100 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 144 h 3.1: Br₂ / diethyl ether / 0 °C 3.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 4.1: 90 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 36 h 5.1: Br₂ / diethyl ether / 0.5 h / 0 °C 5.2: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C

Multi-step reaction with 3 steps 1.1: Br₂ / diethyl ether / 0 °C 1.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 2.1: 100 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 144 h 3.1: Br₂ / diethyl ether / 0.5 h / 0 °C 3.2: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C

Reference： [1]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[2]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[3]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[4]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]

39
[ 1485-07-0 ]
[ 374928-94-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: Br₂ / diethyl ether / 0 °C 1.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 2.1: 90 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 36 h 3.1: Br₂ / diethyl ether / 0.5 h / 0 °C 3.2: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C 4.1: 99 percent / H₂SiF₆ / acetonitrile; various solvent(s) / 24 h 5.1: Br₂ / diethyl ether / 0 °C 5.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C
	Multi-step reaction with 3 steps 1.1: Br₂ / diethyl ether / 0 °C 1.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 2.1: 90 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 36 h 3.1: Br₂ / diethyl ether / 0 °C 3.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C
	Multi-step reaction with 5 steps 1.1: Br₂ / diethyl ether / 0.5 h / 0 °C 1.2: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C 2.1: 99 percent / H₂SiF₆ / acetonitrile; various solvent(s) / 24 h 3.1: Br₂ / diethyl ether / 0 °C 3.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C 4.1: 90 percent / H₂SiF₆ / methanol; acetonitrile; various solvent(s) / 36 h 5.1: Br₂ / diethyl ether / 0 °C 5.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C

Multi-step reaction with 3 steps 1.1: Br₂ / diethyl ether / 0.5 h / 0 °C 1.2: 2.0 g / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C 2.1: 99 percent / H₂SiF₆ / acetonitrile; various solvent(s) / 24 h 3.1: Br₂ / diethyl ether / 0 °C 3.2: 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 0 °C

Reference： [1]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[2]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[3]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]
[4]Nakamura; Linclau; Curran [Journal of the American Chemical Society, 2001, vol. 123, # 41, p. 10119 - 10120]

40
[ 1485-07-0 ]
[ 150255-97-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.92 h / 0 - 20 °C 2: 1.) NaH / 1.) THF, 0 deg C, 10 min, 2.) THF, 30 min 3: 99 percent / H₂ / 5percent Pd/C / ethanol / 0.75 h / 2585.7 Torr

Reference： [1]Ellingboe, John W.; Lombardo, Louis J.; Alessi, Thomas R.; Nguyen, Thomas T.; Guzzo, Frieda; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 17, p. 2485 - 2493]

41
[ 1485-07-0 ]
N-Hydroxy-4-naphthalen-2-yl-butyramidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.92 h / 0 - 20 °C 2: 1.) NaH / 1.) THF, 0 deg C, 10 min, 2.) THF, 30 min 3: 99 percent / H₂ / 5percent Pd/C / ethanol / 0.75 h / 2585.7 Torr 4: NH₂OH*HCl, NaOMe / methanol; dimethylsulfoxide / 1.5 h / 80 °C

Reference： [1]Ellingboe, John W.; Lombardo, Louis J.; Alessi, Thomas R.; Nguyen, Thomas T.; Guzzo, Frieda; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 17, p. 2485 - 2493]

42
[ 1485-07-0 ]
4-(3-Naphthalen-2-yl-propyl)-3H-[1,2,3,5]oxathiadiazole 2-oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.92 h / 0 - 20 °C 2: 1.) NaH / 1.) THF, 0 deg C, 10 min, 2.) THF, 30 min 3: 99 percent / H₂ / 5percent Pd/C / ethanol / 0.75 h / 2585.7 Torr 4: NH₂OH*HCl, NaOMe / methanol; dimethylsulfoxide / 1.5 h / 80 °C 5: SOCl₂, pyridine / CH₂Cl₂ / 0.42 h

Reference： [1]Ellingboe, John W.; Lombardo, Louis J.; Alessi, Thomas R.; Nguyen, Thomas T.; Guzzo, Frieda; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 17, p. 2485 - 2493]

43
[ 1485-07-0 ]
[ 157942-12-6 ]
[ 1192491-38-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; at 20℃; for 12h;	A solution of the compound prepared in Reference Example 2 (3.00 g), 2-(2-naphthyl)ethanol (2.23 g), triphenylphosphine (4.25 g) and 1,1'-(azodicarbonyl)dipiperidine (4.09 g) in anhydrous tetrahydrofuran (50 ml) was stirred at room temperature for 12 hours under an atmosphere of argon. The mixture was diluted with diethyl ether and filtered. The filtrate was concentrated. The residue was purified by column chromatography (n-hexane : ethyl acetate =20 : 1 ? 10 : 1 ? 5 : 1) to give the title compound (4.64 g) having the following physical data. TLC: Rf 0.54 (n-hexane : ethyl acetate = 4 : 1).

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 6567 - 6582
[2]Patent: EP1431267,2004,A1 .Location in patent: Page 50

44
[ 499157-55-0 ]
[ 1485-07-0 ]
[ 499157-57-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃;	31 Reference Example 31; 4-phenoxymethyl-2-[N-[2-(naphthalen-2-yl)ethyl]-N-2-nitrophenylsulfonylamino]phenyl iodide To a solution of the compound prepared in Reference Example 30 (788 mg) and 2-(naphthalen-2-yl)ethanol (385 mg) in tetrahydrofuran (5.0 ml) were added diethylazodicarboxylate (0.97 ml) and triphenylphosphine (585 mg) at room temperature. The mixture was stirred overnight. The reaction mixture was concentrated and the residue was purified by column chromatography on silica gel (n-hexane : ethyl acetate = 3 : 1) to give the title compound having the following physical data. TLC: Rf 0.47 (n-hexane : ethyl acetate = 2 : 1); NMR (300MHz, CDCl3): δ 7.88-7.11 (m, 16H), 7.04-6.85 (m, 3H), 6.87 (d, J = 12.3 Hz, 1H), 4.80 (d, J = 12.3 Hz, 1H), 4.40 (m, 1H), 3.89 (m, 1H), 3.18-3.00 (m, 2H).

Reference： [1]Current Patent Assignee: ONO PHARMACEUTICAL CO LTD - EP1431267, 2004, A1 Location in patent: Page 540

45
[ 566189-20-6 ]
[ 1485-07-0 ]
ST 2167 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61.2%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃;	10 Example 10 Preparation of methyl 2-[3-[2-(2-naphthyl)ethoxy]phenylthio]iso- butyrate (ST2167) The product was prepared according to the procedure described in Method B (with the exception of DEAD which was replaced by DIAD) starting from methyl 2- (3-hydroxyphenylthio) isobutyrate (prepared as described in example 1) (1.110 g, 4.9 mmol), 2- (2- naphthyl) ethanol (0.842 g, 4.9 mmol), DIAD (1.290 g, 6.37 mmol), and triphenylphosphine (1.670 g, 6.37 mmol) in 20 mL of anhydrous THF. The reaction was left overnight under magnetic stirring at room temperature. After this period, the solvent was evaporated and the residue purified by silica gel chromatography using hexane/AcOEt 7/3 as eluent. The product was further purified by dissolving it in ethyl acetate and washing the organic phase with a solution of NA2CO3. The organic phase was dried on sodium sulphate and the solvent evaporated in vacuo. 1.14 g of product were obtained (yield : 61.2%) ; TLC: silica gel, eluent hexane/AcOEt 9/1, Fr: 0.20 ; 1H NMR (CDC13, 300 MHz) 5 : 7.80 (M, 3H), 7.75 (s, 1H), 7.45 (m, 3H), 7.25 (T, 1H), 7.05 (m, 2H), 6.90 (d, 1H), 4.25 (t, 2H), 3.65 (s, 3H), 3.30 (t, 2H), 1.50 (s, 6H); HPLC: Column: Inertisil ODS-3 (5PM) 4.6 x 250 mm, T: room temperature, mobile phase CH3CN/H20 80/20 (v/v), pH: as is, flow rate: 0.9 mL/min, 205 nm UV detector, retention time 18.91 min; KF : 1. 0 % H20 ; E. A. conforming for C23H2403S.

Reference： [1]Current Patent Assignee: ALFASIGMA GROUP - WO2004/56355, 2004, A1 Location in patent: Page/Page column 25-26

46
[ 566189-18-2 ]
[ 1485-07-0 ]
methyl 2-[4-[2-(2-naphthyl)ethoxy]phenylthio]isobutyrate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20 - 30℃;	11 Example 11 Preparation of methyl 2- [4- [2- (2-NAPHTHYL) ETHOXY] PHENYLTHIO] ISO- BUTYRATE (ST2011) The product was prepared according to the procedure described in Method B starting from methyl 2- (4-hydroxyphenylthio) isobutyrate (prepared as described in example 3) (1.000 g, 4.42 mmol), 2- (2-NAPHTHYL) ethanol (0.760 g, 4.42 mmol), DEAD (1.000 g, 5.75 mmol) and triphenylphosphine (1.500 g, 5.75 mmol) added piecemeal in small portions, maintaining the temperature below 30°C, in 30 mL of anhydrous THF. The reaction was left overnight under magnetic stirring at room temperature. After this period, the solvent was evaporated and the residue purified by silica gel chromatography using hexane/AcOEt 9/1 as eluent. 1.262 g of product (yield: 75%); Mp: 56-57°C ; TLC: silica gel, eluent hexane/AcOEt 9/1, Fr: 0.23 ; 1H NMR (CDCl3, 300 MHz) 8 7.85- 7.70 (m, 4H), 7.45-7. 28 (m, 5H), 6.83 (d, 2H), 4.27 (t, 2H), 3.65 (s, 3H), 3.26 (t, 2H), 1.45 (s, 6H); HPLC: Column: Inertisil ODS-3 (5 ; J. M) 4.6 x 250 mm, T: room temperature, mobile phase CH3CN/H20 80/20 (v/v), pH: as is, flow rate: 0.75 mL/min, 205 nm UV detector, retention time 23.51 min; KF: 0.16 % H20; E. A. conforming for C23H2403S.

Reference： [1]Current Patent Assignee: ALFASIGMA GROUP - WO2004/56355, 2004, A1 Location in patent: Page/Page column 26-27

47
[ 1485-07-0 ]
[ 4124-41-8 ]
[ 7175-35-1 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In tetrahydrofuran at 20℃; for 1h;	B.56 Toluene-4-sulfonic acid 2-naphthalen-2yl-ethyl ester To a solution of 2-naphthalen-2yl-ethanol (3.0 g, 17.4 mmoles) in tetrahydrofuran (50 ml), is added para-toluenesulfonic anhydride (6.8 g, 1.2 eq), and triethylamine (7.1 ml, 3 eq). The resulting solution is stirred at room temperature for one hour and then the solvents are removed under reduced pressure. The crude material is purified by flash chromatography on silica gel (20% ethyl acetate/hexane) to afford the title compound.

Reference： [1]Current Patent Assignee: PROCTER & GAMBLE CO - US2006/128613, 2006, A1 Location in patent: Page/Page column 24

48
[ 330193-64-1 ]
[ 1485-07-0 ]
[ 70080-13-6 ]
2-amino-6-(4-methoxy-benzyl)-5-((2-naphthalen-2-yl-ethylamino)-methyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 2.5h;	32 A solution of 2-naphthalen-2-yl-ethanol (1.02 g, 5.8 mmol), 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) (9 mg, 0.058 mmol) and sodium bromide (0.65 g, 6.4 mmol) in a mixture of toluene (18 mL), ethyl acetate (18 mL), and water (3mL) was cooled to 0 °C and added dropwise over 1 hour a solution containing the following: sodium hypochlorite (17.2 mL, 0.37 M, 6.4 mmol) and sodium hydrogencarbonate (1.46 g, 17.4 mmol). The reaction mixture was stirred at 0 °C for 10 min., and the phases separated. The aqueous layer was extracted with ethyl acetate (150 mL). The combined organic phases were washed with a solution of potassium iodone (0.2 g) in 10 % aqueous potassium hydrogensulfate (150 mL), water (150 mL), brine (150 mL), dried (MgSO4), filtered, and concentrated in vacuo to provide 980 mg of a 3:1 mixture of naphthalen-2-yl-acetaldehyde and 2-naphthalen-2-yl-ethanol. 1H-NMR (CDCl3): δ 9.81 (t, 1H, J = 1.5 Hz), 7.92-7.80 (m, 3H), 7.68 (bs, 1H), 7.55-7.42 (m, 3H), 3.87 (d, 2H, J = 1.5 Hz). To a solution of 2-amino-5-aminomethyl-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester (290 mg, 0.71 mmol) in 1,2-dichloroethane (3 ml) was added the above mixture of 2-naphthyl-acetaldehyde (100 mg, 0.59 mmol), sodium triacetoxyborohydride (190 mg, 0.88 mmol) and the mixture was stirred at room temperature under nitrogen for 2.5 hours. The crude reaction mixture was quenched with saturated sodium bicarbonate (50 ml) and the solution extracted with ethyl acetate (100 ml). The organic phase was dried (MgSO4), filtered, and concentrated in vacuo providing a foam, which was taken directly to the next step. LC-MS showed that 2-amino-6-(4-methoxy-benzyl)-5-((2-naphthalen-2-yl-ethylamino)-methyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester was the major component. LC-MS: m/z: 558.1 [M+H]+, Rf = 2.23 min. To a solution of 2-amino-6-(4-methoxy-benzyl)-5-((2-naphthalen-2-yl-ethylamino)methyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester in tetrahydrofuran (3 ml) was added di-tert-butyl-dicarbonate (188 mg, 0.85 mmol) and N,N-dimethylformamide (18 mg, 0.14 mmol). The reaction was stirred at room temperature for 7 hours under nitrogen. The crude reaction mixture was diluted with dichloromethane (50 ml) and washed with water (50 ml) and brine (50 ml). The organic phase was dried (MgSO4), filtered, and concentrated in vacuo affording a foam, which was used without further purification in the next step. LC-MS showed that 2-amino-5-((tert-butoxycarbonyl-(2-naphthalen-2-yl-ethyl)-amino)-methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester was the major component. Rf= 2.74, m/z: 658.1 [M+H]+, Calculated: 657.4. To crude 2-amino-5-((tert-butoxycarbonyl-(2-naphthalen-2-yl-ethyl)-amino)-methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester was added dichloromethane (5 ml) and imidazol-1-yl-oxo-acetic acid tert-butyl ester (400 mg, 1.78 mmol) and the reaction mixture stirred at room temperature for 12 hours. The crude reaction mixture was added to dichloromethane (50 ml) and washed with water (50 ml) and brine (50 ml). The organic phase was dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography using a mixture of dichloromethane/ethyl acetate (10:1) as eluent, which afforded 20.3 mg (39 % over tree steps) of 2-(tert-butoxyoxalyl-amino)-5-((tert-butoxycarbonyl-(2-naphthalen-2-yl-ethyl)-amino)methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester as a foam. 1H NMR (CDCl3) δ 7.99-7.92 (m, 3H), 7.88 (s, 1H), 7.68-7.57 (m, 3H), 7.45 (d, 2H, J = 7.8 Hz), 6.99 (d, 2H, J = 8.1 Hz), 3.90-3.75 (m, 7H), 3.56-3.42 (m, 5H), 3.19-3.13 (m, 2H), 2.88-2.82 (m, 2H), 1.79 (s, 9H), 1.71 (s, 18H); LC-MS: m/z: 786.2 [M+H]+, Rf = 3.03 min. To a solution of 2-(tert-butoxyoxalyl-amino)-5-((tert-butoxycarbonyl-(2-naphthalen-2-yl-ethyl)-amino)methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester (20 mg, 0.03 mmol) in dry dichloromethane (200 µl) at 0 °C was added 50 % trifluoroacetic acid in dichloromethane (2.5 ml). The reaction was stirred for 14 hours at room temperature and then concentrated in vacuo. The resultant solid was resuspended in dichloromethane, filtered, and dried in vacuo to provide 13 mg (90 %) of the title compound as a solid. 1H NMR (DMSO-d6) δ 9.15 (s, 1H), 8.09-8.01 (m, 3H), 7.93 (s, 1H), 7.68-7.57 (m, 3H), 7.45 (d, 2H, J =7.8 Hz), 6.99 (d, 2H, J = 8.1 Hz), 4.18-4.12 (m, 2H), 3.90-3.75 (m, 7H), 3.56-3.42 (m, 3H), 3.19-3.13 (m, 2H), 2.88-2.82 (m, 2H); LC-MS: m/z: 574.7 [M+H]+, Rf = 1.36 min.

Reference： [1]Current Patent Assignee: NOVO NORDISK A/S; ONTOGEN CORP - EP1214324, 2006, B1 Location in patent: Page/Page column 49-50

49
1,8-diazaabicyclo[5.4.0]undec-7-ene [ No CAS ]
[ 1485-07-0 ]
[ 2017-67-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	With diphenylphosphoranyl azide; triphenylphosphine In tetrahydrofuran; diethyl ether; ethanol; N,N-dimethyl-formamide	1 2-Naphth-2-ylethylamine EXAMPLE 1 2-Naphth-2-ylethylamine A solution comprising 2-naphth-2-ylethanol (0.5 g, 2.9 mmol) in dry DMF (5 mL) was combined under nitrogen with diphenylphosphoryl azide (0.74 mL, 3.42 mmol) and 1,8-diazaabicyclo[5.4.0]undec-7-ene (0.47 mL. 3.14 mmol). The mixture was heated at 65° C. for 3 hours and then partitioned between water and diethyl ether. The aqueous layer was separated and extracted with diethyl ether. The combined organic layers were washed with 3N hydrochloric acid and then saturated sodium bicarbonate, dried (MgSO4), filtered and concentrated by rotary evaporation. The residue was dissolved in THF (5 mL) and the solution was combined with triphenylphosphine (1 g, 3.81 mmol), stirred for 2 hours at room temperature, diluted with water (0.100 mL), stirred 3 hours, diluted with concentrated hydrochloric acid (0.33 mL) to give a precipitate, treated with ethanol (5 mL) to dissolve the precipitate and treated with diethyl ether, added slowly, to give a white precipitate. The while precipitate was isolated by filtration, washed with diethyl ether and dried under vacuum to provide 2-naphth-2-ylethylamine hydrochloride (0.447 g, 75% yield); 1H-NMR (300 Mhz, DMSO-d6): 8.18 (br s, 3H), 7.82-7.88 (m, 3H), 7.74 (s, 1H), 7.38-7.48 (m, 3H), 3.07 (m, 4H).

Reference： [1]Current Patent Assignee: QUEST DIAGNOSTICS INC - US2001/53779, 2001, A1

50
[ 288-32-4 ]
[ 1485-07-0 ]
[ 2086-62-6 ]

Yield	Reaction Conditions	Operation in experiment
86%	With N-Bromosuccinimide; triphenylphosphine In dichloromethane	125.1 N-Hydroxy-5-N-[2-(2-naphthylethyl)-methylamino]pentanamide (216) Step 1: 2-(2-Bromoethyl)naphthalene (214) A solution of triphenylphosphine (0.57 g, 2.2 mmol) and N-bromosuccinimide (0.39 g, 2.2 mmol) in anhydrous dichloromethane (4 mL) was stirred for 10 minutes. 2-Naphthalenethanol (0.25 g, 1.45 mmol) was added, followed immediately by imidazole (0.25 g, 1.45 mmol) and the mixture was stirred at room temperature for 18 hours. The reaction mixture was partitioned between H2O and dichloromethane. The aqueous layer was extracted with diethyl ether (2*20 mL) and the combined organic extracts were dried over MgSO4 and evaporated to dryness. The crude residue was purified by column chromatography through a plug of silica gel eluding with 10% ethyl acetate in hexanes to afford a colorless solid 214 (0.29 g, 86%).

Reference： [1]Current Patent Assignee: MIRATI THERAPEUTICS, INC. - US2002/115826, 2002, A1

51
[ 1485-07-0 ]
[ 24589-98-8 ]
[ 908296-34-4 ]

Reference： [1]Patent: WO2006/90850,2006,A1 .Location in patent: Page/Page column 65

52
[ 1485-07-0 ]
[ 115351-61-6 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide In tetrachloromethane; diethyl ether; acetonitrile	P.3 SYNTHESIS OF 3-(2-TRIETHYLSILANYLOXY-ETHYL)-1,8-NAPHTHOSULTAM STR276 Step 1: 1-Bromo-2-(2-hydroxy-ethyl)-naphthalene A solution of 2-(2-hydroxy-ethyl)-naphthalene (58.5 g, 0.34 mol) in anhydrous acetonitrile (500 mL) was treated with N-bromo-succinimide (66.5 g, 0.37 mol). The resulting solution was stirred at room temperature under a nitrogen atmosphere and protected from light for 30 minutes, then heated in an oil bath at 50° C. for 2 hours. After cooling to room temperature, the reaction mixture was evaporated under vacuum to a viscous oil. The oil in diethyl ether (350 mL) was washed with water (350 mL), dilute aqueous sodium thiosulfate (300 mL), water (300 mL) and brine (200 mL), dried over magnesium sulfate, filtered, and evaporated under vacuum to an oil (89.5 g) that solidified on standing. The crude product was chromatographed on a column of EM silica gel 60, eluding with methylene chloride, to afford a yellow solid (78.2 g). Recrystallization of this material from carbon tetrachloride provided the title compound (46.5 g) as a pale yellow solid.
	With N-Bromosuccinimide In tetrachloromethane; diethyl ether; acetonitrile	P.2.1 Step 1: Step 1: 1-Bromo-2-(2-hydroxy-ethyl)-naphthalene A solution of 2-(2-hydroxy-ethyl)-naphthalene (58.5 g, 0.34 mol) in anhydrous acetonitrile (500 mL) was treated with N-bromo-succinimide (66.5 g, 0.37 mol). The resulting solution was stirred at room temperature under a nitrogen atmosphere and protected from light for 30 minutes, then heated in an oil bath at 50°C for 2 hours. After cooling to room temperature, the reaction mixture was evaporated under vacuum to a viscous oil. The oil in diethyl ether (350 mL) was washed with water (350 mL), dilute aqueous sodium thiosulfate (300 mL), water (300 mL) and brine (200 mL), dried over magnesium sulfate, filtered, and evaporated under vacuum to an oil (89.5 g) that solidified on standing. The crude product was chromatographed on a column of EM silica gel 60, eluding with methylene chloride, to afford a yellow solid (78.2 g). Recrystallization of this material from carbon tetrachloride provided the title compound (46.5 g) as a pale yellow solid.
	With N-Bromosuccinimide In tetrachloromethane; diethyl ether; acetonitrile	P.3.1 Step 1: Step 1: 1-Bromo-2-(2-hydroxy-ethyl)naphthalene A solution of 2-(2-hydroxy-ethyl)-naphthalene (58.5 g, 0.34 mol) in anhydrous acetonitrile (500 mL) was treated with N-bromo-succinimide (66.5 g, 0.37 mol). The resulting solution was stirred at room temperature under a nitrogen atmosphere and protected from light for 30 minutes, then heated in an oil bath at 50° C. for 2 hours. After cooling to room temperature, the reaction mixture was evaporated under vacuum to a viscous oil. The oil in diethyl ether (350 mL) was washed with water (350 mL), dilute aqueous sodium thiosulfate (300 mL), water (300 mL) and brine (200 mL), dried over magnesium sulfate, filtered, and evaporated under vacuum to an oil (89.5 g) that solidified on standing. The crude product was chromatographed on a column of EM silica gel 60, eluding with methylene chloride, to afford a yellow solid (78.2 g). Recrystallization of this material from carbon tetrachloride provided the title compound (46.5 g) as a pale yellow solid.

Reference： [1]Current Patent Assignee: MERCK & CO INC - US6140318, 2000, A
[2]Current Patent Assignee: MERCK & CO INC - EP1023062, 2002, B1
[3]Current Patent Assignee: MERCK & CO INC - US6294529, 2001, B1

53
4-chloro-4'-fluorobutyrophenone-2,2-dimethylpropylene ketal [ No CAS ]
[ 1485-07-0 ]
1-(4-Fluorophenyl)-4-[2-(2-naphthalenyl)ethoxy]-1-butanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With hydrogenchloride In methanol; N,N-dimethyl-formamide	4.A A. A. 1-(4-Fluorophenyl)-4-[2-(2-naphthalenyl)ethoxy]-1-butanone A suspension of 4-chloro-4'-fluorobutyrophenone-2,2-dimethylpropylene ketal (28.7 g, 0.1 mole) and sodium hydride (2.6 g, 0.11 mole) in dry N,N-dimethylformamide (50 ml) was treated dropwise with a solution of 2-naphthaleneethanol (17.2 g, 0.1 mole) in dry N,N-dimethylformamide (50 ml). The reaction mixture was stirred at room temperature for one hour and refluxed under dry nitrogen for 16 hours. The mixture was concentrated in vacuo, and the residue was partitioned between diethyl ether (200 ml) and sodium bicarbonate (5%, 200 ml). The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to an impure oil as indicated by tlc (chloroform-methanol, 9:1). The impure ketal was dissolved in methanol (100 ml) and treated with concentrated hydrochloric acid (50 ml) and stirred at room temperature until no starting ketal was evidenced by tlc (chloroform-methanol, 9:1). The reaction mixture was diluted with water (200 ml) and extracted with diethyl ether (200 ml). The ethereal extract was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to an oil. The oil was column chromatographed on silica gel (n-butyl chloride). Appropriate fractions were combined and concentrated in vacuo to give a solid which was recrystallized from ethanol to yield the title compound (21.2 g, 63%); mp 68°-70° C.; IR(nujol): C=O ã 1679 cm-1; NMR(CDCl3, TMS): δ2.0(d of t,2H,CH2), 2.93(t,2H,CH2 --CO), 3.03(t,2H,ArCH2), 3.53,3.73(2t,4H,CH2 --O--CH2), 6.9-8.0(m,11H,aromatic); Anal. Calcd. for C22 H21 FO2, MW 336.40: C,78.55; H,6.92. Found: C,78.18; H,6.33. Mass spectrum m/e 336,154.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US5039706, 1991, A

54
[ 1485-07-0 ]
[ 33953-37-6 ]
[ 36793-42-7 ]

Yield	Reaction Conditions	Operation in experiment
	In 5,5-dimethyl-1,3-cyclohexadiene	61 4-Benzamido-1-[2-(2-naphthyl)ethyl]piperidine EXAMPLE 61 4-Benzamido-1-[2-(2-naphthyl)ethyl]piperidine 2-(2-Naphthyl)ethanol (3.44 g., 0.02 mole), 4-benzamidopiperidine (4.08 g.,0.02 mole) and Raney Nickel (W7 ca. 5 g.) were suspended in xylene (200 ml.) and the stirred mixture boiled under reflux for 16 hours. Liberated water was removed by means of a Dean and Stark apparatus. The mixture was filtered hot and evaporated to ca. 100 ml. The resulting yellow solution was stored until crystallisation was complete. The title compound was obtained as off-white needles (3.30 g.), m.p. 189°-191° C.
	In 5,5-dimethyl-1,3-cyclohexadiene	61 4-Benzamido-1-[2-(2-naphthyl)ethyl]piperidine EXAMPLE 61 4-Benzamido-1-[2-(2-naphthyl)ethyl]piperidine 2-(2-Naphthyl)ethanol (3.44 g., 0.02 mole), 4-benzamidopiperidine (4.08 g., 0.02 mole) and Raney Nickel (W7 ca. 5 g.) were suspended in xylene (200 ml.) and the stirred mixture boiled under reflux for 16 hours. Liberated water was removed by means of a Dean and Stark apparatus. The mixture was filtered hot and evaporated to ca. 100 ml. The resulting yellow solution was stored until crystallisation was complete. The title compound was obtained as off-white needles (3.30 g.), m.p. 189°-191° C.

Reference： [1]Current Patent Assignee: PFIZER INC - US3992389, 1976, A
[2]Current Patent Assignee: PFIZER INC - US4029801, 1977, A

55
[ 1485-07-0 ]
[ 581-96-4 ]

Yield	Reaction Conditions	Operation in experiment
86 % Chromat.	With NADH oxidase; nicotinamide adenine dinucleotide at 25℃; for 12h;

Reference： [1]Hirano, Jun-ichiro; Miyamoto, Kenji; Ohta, Hiromichi [Tetrahedron Letters, 2008, vol. 49, # 7, p. 1217 - 1219]

56
C₁₁H₂₁NO₄S [ No CAS ]
[ 1485-07-0 ]
(1R,2R)/(1S,2S)-1-(2-naphthalenethoxy)-2-(4-morpholinyl)cyclohexane monohydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	Stage #1: naphthalen-2-ethanol With sodium hydride In DMF (N,N-dimethyl-formamide) at 20℃; Stage #2: C₁₁H₂₁NO₄S In DMF (N,N-dimethyl-formamide) at 40 - 80℃; Stage #3: With hydrogenchloride In diethyl ether	1.iii EXAMPLE I(+/-)-TRANS-[2-(4-MORPHOLINYL)-1-(2-NAPHTHENETHOXY)]CYCLOHEXANE MONOHYDROCHLORIDE (COMPOUND No.1) (iii) To sodium hydride, 80% oil dispersion previously washed with hexanes (3 x 20 mL), (1.24 g, 51.6 mmol) in dry dimethylformamide (50 mL) was added via cannula a solution of 2-naphthenethanol (6.8 'g, 40 mmol) in dry dimethylformamide (50 mL). Addition was followed by gas evolution and, as the reaction mixture was stirred at room temperature, it began to gel. The mesylate as prepared in (ii) above was dissolved in dimethylformamide (50 mL) and the resulting solution was added quickly via cannula to the slurry of alcoholate. The reaction mixture was heated to 80C and then the temperature reduced to 40C. The resulting yellow solution was poured into ice-water (1500 mL) and extracted with ethyl acetate (3 x 300 mL). The combined organic extracts were backwashed with a saturated aqueous solution of sodium chloride (500 mL) and dried over sodium sulfate. Evaporation of the solvent in vacuo provided 13.4 g of an amber oil which was dissolved in water (150 mL) and the pH of the solution was adjusted to pH 2 with aqueous 1M HCl. The acidic aqueous solution was extracted with ethyl ether (2 x 100 mL) and then basified to pH 10 with 50% sodium hydroxide aqueous solution. The basic aqueous solution was extracted with ethyl ether (2 x 100 mL), the combined organic layers were dried over sodium sulfate and concentrated in vacuo to leave 7.16 g of the crude free aminoether. The crude product was purified by chromatography on silica gel 60 (70-230 mesh) with a mixture of ethyl acetate-chloroform (1: 1, v/v) as eluent to yield 4.37 g of the pure free base. The product was dissolved in ethyl ether (80 mL) and converted to the monohydrochloride salt by adding saturated solution of HCl in ethyl ether (80 mL). An oil came out of the solution, the solvent was evaporated in vacuo and the residue dissolved in the minimum amount of warm ethyl alcohol, addition of a large volume of ethyl ether triggered crystallization. The crystals were collected to afford 3.83 g (31% yield) of the title compound, m.p. 158-160C, having the elemental analysis indicated in Table 1.

Reference： [1]Current Patent Assignee: NORDIC CAPITAL PARTNERS II AS - EP1087934, 2004, B1 Location in patent: Page 19-20

57
C₁₃H₂₄N₂O₄S [ No CAS ]
[ 1485-07-0 ]
(1R,2R)/(1S,2S)-1-(2-naphthalenethoxy)-2-(1-acetylpiperazinyl)cyclohexane monohydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: naphthalen-2-ethanol With sodium hydride In DMF (N,N-dimethyl-formamide) at 20℃; for 0.5h; argon atmosphere; Stage #2: C₁₃H₂₄N₂O₄S In DMF (N,N-dimethyl-formamide) at 80℃; for 16h; Stage #3: With hydrogenchloride In diethyl ether	16.iii EXAMPLE 16(1R,2R)/(1S,2S)-2-(1-ACETYLPIPERAZINYL)-1-(2-NAPHTHENETHOXY)CYCLOHEXANE MONOHYDROCHLORIDE (COMPOUND No.16) (iii) To a suspension of sodium hydride (0.8 g, 24 mmol, previously washed with hexanes (2 x 15 mL)) in anhydrous dimethylformamide (50 mL) was added a solution of 2-naphthenethanol in anhydrous dimethylformamide (50 mL). The resulting mixture was stirred at room temperature for 30 min.(iv) (1R,2R)/(1S,2S)-2-(1-Acetylpiperazinyl)-1-(2-naphthenethoxy)cyclohexane monohydrochloride: the mesylate (ii) in solution in anhydrous dimethylformamide (50 mL) was added quickly to the alkoxide mixture (iii) and the resulting mixture was heated to 80°C for 16 hours. The cooled reaction mixture was poured into ice water (800 mL) and extracted with ethyl acetate (3 x 200 mL). The combined organic extracts were back-washed with brine (200 mL) and the solvent was evaporated in vacuo. The residual oil was taken up with water (80 mL) and the resulting aqueous solution was acidified to pH 2 with 6M HCl aqueous solution. The acidic aqueous solution was extracted with diethyl ether (3 x 40 mL) in order to extract the unreacted 2-naphthenethanol. The pH of the aqueous layer was adjusted to pH10 with 50% NaOH aqueous solution and extracted with diethyl ether (3 x 40 mL). The combined organic extracts were dried over sodium sulfate and the solvent was evaporated in vacuo to yield the crude free aminoether. Purification by column chromatography of silica gel using a mixture of ethyl acetate-dichloromethane (1:1, v/v) as eluent provided the pure free base. Conversion to the hydrochloride salt was accomplished with ethereal HCl followed by recrystallization in a mixture of ethanol-diethyl ether provided the title compound, having the elemental analysis indicated in Table 1.

Reference： [1]Current Patent Assignee: NORDIC CAPITAL PARTNERS II AS - EP1087934, 2004, B1 Location in patent: Page 27

58
[ 1485-07-0 ]
[ 2524-64-3 ]
[ 1063708-04-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine In tetrahydrofuran for 8h; Inert atmosphere; Reflux;
	With triethylamine In tetrahydrofuran Inert atmosphere; Reflux;

Reference： [1]Location in patent: experimental part Murai, Toshiaki; Tonomura, Yusuke; Takenaka, Toru [Heteroatom Chemistry, 2011, vol. 22, # 3-4, p. 417 - 425]
[2]Murai, Toshiaki; Takenaka, Tohru; Inaji, Shinsuke; Tonomura, Yusuke [Chemistry Letters, 2008, vol. 37, # 12, p. 1198 - 1199]

59
[ 1485-07-0 ]
[ 1192139-91-5 ]
[ 1192139-92-6 ]

Yield	Reaction Conditions	Operation in experiment
32%	With triethylamine In dichloromethane at 0 - 20℃;	1 Synthesis of 2-(naphthalen-2-yl)ethyl 4-(methyl(prop-2-ynyl)carbamoyl)benzenesulfonate (4) 3 (2.5 g, 9.2 mmol) and naphthylethanol (1.9 g, 11.0 mmol) were dissolved in DCM (5 mL). At 0°C 1 crystal of DMAP (ca. 1 mg) was added and then triethylamine (2.58 mL, 1.85 g, 18.4 mmol) was added dropwise. After stirring at ambient temperature for 24h the solvents were evaporated in vacuo at <30°C to give crude 4 (5.85 g, max. 9.2 mmol, quant.). Pure 4 (1.18 g, 2.9 mmol, 32%) was isolated by automated column chromatography (SiO2, 0-10% methanol in DCM).

Reference： [1]Current Patent Assignee: LIFE HEALTHCARE GROUP HOLDINGS (PTY) LTD - EP2110367, 2009, A1 Location in patent: Page/Page column 22

60
[ 1485-07-0 ]
[ 52085-14-0 ]
[ 1192491-32-9 ]

Yield	Reaction Conditions	Operation in experiment
73%	With triphenylphosphine; 1,1'-azodicarbonyl-dipiperidine In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Asada, Masaki; Obitsu, Tetsuo; Nagase, Toshihiko; Sugimoto, Isamu; Yamaura, Yoshiyuki; Sato, Kazutoyo; Narita, Masami; Ohuchida, Shuichi; Nakai, Hisao; Toda, Masaaki [Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 18, p. 6567 - 6582]

61
[ 1485-07-0 ]
[ 98-59-9 ]
[ 7175-35-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	With trimethylamine hydrochloride; triethylamine at 0℃; for 1h; Inert atmosphere;	4.1.42. 2-(2-Chloro-4-methoxyphenyl)ethyl 4-methylbenzenesulfonate (14a) General procedure: To a mixture of intermediate 13a (1.20 g, 6.43 mmol), triethylamine(1.08 mL, 7.72 mmol) and trimethylamine hydrochloride(61.5 mg, 0.643 mmol) in CH2Cl2 (12 mL) was added p-toluenesulfonylchloride (1.35 g, 7.07 mmol) at 0 C. After stirring at 0 C for1 h, the reaction mixture was treated with H2O (50 mL) andextracted with CHCl3 (30 mL 2). The organic layer was dried overMgSO4, filtered and concentrated in vacuo. The residue was purifiedby silica gel chromatography using 4 25% EtOAc/hexane aseluent to give 2.08 g (95%) of the title compound as a colorlessoil.
	With dmap; triethylamine In dichloromethane Inert atmosphere;

Reference： [1]Yoshinaga, Hidefumi; Masumoto, Shuji; Koyama, Koji; Kinomura, Naoya; Matsumoto, Yuji; Kato, Taro; Baba, Satoko; Matsumoto, Kenji; Horisawa, Tomoko; Oki, Hitomi; Yabuuchi, Kazuki; Kodo, Toru [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 1, p. 293 - 304]
[2]Location in patent: scheme or table Berhal, Farouk; Perard-Viret, Joelle; Royer, Jacques [Tetrahedron Asymmetry, 2010, vol. 21, # 3, p. 325 - 332]

62
[ 1191-99-7 ]
[ 253-52-1 ]
[ 1485-07-0 ]

Yield	Reaction Conditions	Operation in experiment
43%	With 5,10-dimethyl-5,10-dihydroboranthrene pthalizine complex; N-ethyl-N,N-diisopropylamine In diethylene glycol dimethyl ether at 170℃; for 72h;
43%	Stage #1: 2,3-dihydro-2H-furan; PHTHALAZINE With N-ethyl-N,N-diisopropylamine; 9,10-dimethyl-9,10-dibora-9,10-dihydroanthracene In diethylene glycol dimethyl ether at 170℃; for 72h; Inert atmosphere; Stage #2: In chloroform-d1 Inert atmosphere; UV-irradiation;
43%	With N-ethyl-N,N-diisopropylamine; 9,10-dimethyl-9,10-dibora-9,10-dihydroanthracene In diethylene glycol dimethyl ether at 170℃; for 72h; Schlenk technique; Inert atmosphere;	General procedure A for IEDDA reactions of phthalazine General procedure: In a Schlenk tube charged with a stirring bar, the air-stable bidentate Lewis acid catalyst B (5.00 mol %) and the stated solvent were added under N2. Then, the phthalazine (1.00 equiv), dienophile (2.00 equiv; for enamines, generated in situ from aldehyde and amine) were added subsequently. The reaction mixture was stirred at the given temperature. After the reaction was finished, the solvent was removed. The remaining residue was purified by flash column chromatography over SiO2 to obtain the product.

Reference： [1]Kessler, Simon N.; Wegner, Hermann A. [Organic Letters, 2010, vol. 12, # 18, p. 4062 - 4065]
[2]Kessler, Simon N.; Neuburger, Markus; Wegner, Hermann A. [European Journal of Organic Chemistry, 2011, # 17, p. 3238 - 3245]
[3]Hong, Longcheng; Ahles, Sebastian; Heindl, Andreas H.; Tiétcha, Gastelle; Petrov, Andrey; Lu, Zhenpin; Logemann, Christian; Wegner, Hermann A. [Beilstein Journal of Organic Chemistry, 2018, vol. 14, p. 618 - 625]

63
[ 1485-07-0 ]
[ 108549-23-1 ]
[ 1301120-91-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: naphthalen-2-ethanol; Dibenzyl N,N-diisopropylphosphoramidite With 1H-tetrazole In dichloromethane at 0 - 20℃; for 3.16667h; Inert atmosphere; Stage #2: With 3-chloro-benzenecarboperoxoic acid In dichloromethane at -40℃; for 1h; Cooling with ice; Inert atmosphere;	To a solution of 2-(naphthalen-2-yl)ethanol (500 mg, 2.90 mmol) and 1H-tetrazole (610mg, 8.71 mmol) in CH2Cl2 (25 mL) was slowly added dibenzyl (N,N-diisopropyl)phosphoramidite (2.01 mL, 5.81 mmol) at 0 °C over a period of 10 min. The mixture was gradually warmed to room temperature, and stirred for 3 h. The mixture was then cooled to -40 °C, and m-CPBA (2.67 g, 75% max., 15.48 mmol) was added. The mixture wasallowed to warm in an ice bath over 1 h. The mixture was diluted with CH2Cl2, washed with saturated Na2S2O3, NaHCO3 (aq), and brine. The organic phase was dried over MgSO4, filtered,and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (EtOAc/hexane = 1:5) to give dibenzyl 2-(naphth-2-yl)ethyl phosphate(1.00g, 80%).

Reference： [1]Lin, Teng-Chi; Fang, Jim-Min [Tetrahedron Letters, 2011, vol. 52, # 17, p. 2232 - 2234]

64
[ 67-56-1 ]
[ 581-96-4 ]
[ 1485-07-0 ]
[ 2876-71-3 ]

Yield	Reaction Conditions	Operation in experiment
1: 50% 2: 28%	Stage #1: 2-naphthylacetic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h; Stage #2: methanol With sodium tetrahydroborate In tetrahydrofuran at 0℃; for 0.5h;

Reference： [1]Location in patent: scheme or table Morales-Serna, Jose Antonio; Garcia-Rios, Erendira; Bernal, Jorge; Paleo, Ehecatl; Gavino, Ruben; Cardenas, Jorge [Synthesis, 2011, # 9, p. 1375 - 1382]

65
[ 1485-07-0 ]
[ 14564-87-5 ]

Yield	Reaction Conditions	Operation in experiment
64%	With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; potassium <i>tert</i>-butylate In para-xylene at 120℃; for 4h; Inert atmosphere;
> 99 %Spectr.	With C₂₈H₃₂IrN₄⁽¹⁺⁾*I^(1-); sodium t-butanolate In tert-Amyl alcohol at 140℃; for 24h; Inert atmosphere;

Reference： [1]Obora, Yasushi; Anno, Yuka; Okamoto, Ryuhei; Matsu-Ura, Toyomi; Ishii, Yasutaka [Angewandte Chemie - International Edition, 2011, vol. 50, # 37, p. 8618 - 8622]
[2]Lu, Zeye; Zheng, Qingshu; Yang, Siqi; Qian, Chun; Shen, Yajing; Tu, Tao [ACS Catalysis, 2021, vol. 11, # 17, p. 10796 - 10801]

66
[ 1485-07-0 ]
[ 66-99-9 ]

Yield	Reaction Conditions	Operation in experiment
35%	With manganese(IV) oxide at 65℃; for 3h;	substrate B (entry 4, Table 3) 344 mg (2 mmol, 1 eq.) 2-(2-naphthyl) ethanol was dissolved in 30 mL PE 60/70 (abs.). 512 mg (4 mmol, 2 eq.)manganese dioxide are added. The black suspension is heated under reflux for 3 h. It was cooled to rt and filtered through Celite. The solvent was then removed. (eluent: cyclohexane:EtOAc = 50: 1 → 20: 1 → 10: 1).1H NMR (300 MHz, CDCl3) δ ppm 7.54 - 7.70 (m, 2 H) 7.88 - 8.07 (m, 4 H) 8.33 - 8.37 (m, 1 H) 10.17 (s, 1 H). 13CNMR (75 MHz, CDCl3) δ ppm 192, 136, 134, 134, 132, 129, 129, 128, 127, 122. FTIR (KBr disc) cm-1 3368, 3065,2847, 2631, 1695, 1656, 1627, 1597, 1578, 1451, 1441, 1403, 1364, 1346, 1267, 1257, 1215, 1167, 1149, 1143,1119, 1008, 986, 955, 909, 879, 872, 837, 822,773, 752, 628, 606, 484, 478. GC/MS-EI m/z(%): 157.1(11),156.1(>100), 155.1(94), 128.1(12), 127.1(60), 126.1(11), 101.1(3), 77.2(4), 75.1(3).
	Multi-step reaction with 2 steps 1: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C / Inert atmosphere 2: tetrafluoroboric acid; iodosylbenzene / 1,4-dioxane; water / 144 h / 20 °C

Reference： [1]Havare, Nizam [Arkivoc, 2020, vol. 2020, # 6, p. 247 - 261]
[2]Havare, Nizam; Plattner, Dietmar A. [Organic Letters, 2012, vol. 14, # 19, p. 5078 - 5081,4]

67
[ 120-72-9 ]
[ 1485-07-0 ]
3-(2-(naphthalen-2-yl)ethyl)-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In o-xylene at 144℃; for 22h; Inert atmosphere; regioselective reaction;

Reference： [1]Siddiki, S. M. A. Hakim; Kon, Kenichi; Shimizu, Ken-Ichi [Chemistry - A European Journal, 2013, vol. 19, # 43, p. 14416 - 14419]

68
[ 1258788-70-3 ]
[ 1485-07-0 ]
[ 1548060-27-0 ]
[ 150256-11-4 ]
[ 91-57-6 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium borohydride; potassium hydroxide In methanol; water at 40℃; for 3h; Sealed tube; Inert atmosphere; Irradiation; Overall yield = 27 %;	4.5.2 General procedures for irradiation in the presence of lithium borohydride in methanol General procedure: Here, the irradiation of 3-(2-naphthalen-1-ylvinyl)furan 1r is used as an example to describe the general experimental procedures, as follows: A total of five identical samples were prepared, each of which contained 1r (20 mg), methanol (18 mL), 50% KOH(aq) (2 mL), and lithium borohydride (40 mg) (CAUTION: the addition of lithium borohydride sometimes causes flames for a short while) in a quartz tube (1.5×20 cm). The tubes were sealed with septa and subjected to sonication to dissolve all of the components. Then, the solution was bubbled with nitrogen gas for 20 min to remove dissolved oxygen. The sample was irradiated with 300 nm UV light at ambient temperature (approximately 40 °C) for a certain time. After irradiation, the five samples were combined, and 500 mL of water was added to the solution. The resulting solution was extracted with ethyl acetate several times, and the organic layers were combined and dried with anhydrous magnesium sulfate. The solvent was removed with a rotary evaporator, and the products were purified via chromatography using a mixed solvent of hexane and ethyl acetate (4:1) for elution. Following chromatography, 4.5 mg of 2r and 44.6 mg of 3r were obtained, and the yields were 5% and 44%, respectively.

Reference： [1]Chen, Ying-Zhe; Ni, Ching-Wen; Teng, Fu-Lin; Ding, Yi-Shun; Lee, Tunng-Hsien; Ho, Jinn-Hsuan [Tetrahedron, 2014, vol. 70, # 9, p. 1748 - 1762]

69
[ 114078-26-1 ]
[ 1485-07-0 ]
[ 91-57-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 30% 2: 7%	With lithium borohydride; potassium hydroxide In methanol; water at 40℃; for 3h; Sealed tube; Inert atmosphere; Irradiation; Overall yield = 37 %;	4.5.2 General procedures for irradiation in the presence of lithium borohydride in methanol General procedure: Here, the irradiation of 3-(2-naphthalen-1-ylvinyl)furan 1r is used as an example to describe the general experimental procedures, as follows: A total of five identical samples were prepared, each of which contained 1r (20 mg), methanol (18 mL), 50% KOH(aq) (2 mL), and lithium borohydride (40 mg) (CAUTION: the addition of lithium borohydride sometimes causes flames for a short while) in a quartz tube (1.5×20 cm). The tubes were sealed with septa and subjected to sonication to dissolve all of the components. Then, the solution was bubbled with nitrogen gas for 20 min to remove dissolved oxygen. The sample was irradiated with 300 nm UV light at ambient temperature (approximately 40 °C) for a certain time. After irradiation, the five samples were combined, and 500 mL of water was added to the solution. The resulting solution was extracted with ethyl acetate several times, and the organic layers were combined and dried with anhydrous magnesium sulfate. The solvent was removed with a rotary evaporator, and the products were purified via chromatography using a mixed solvent of hexane and ethyl acetate (4:1) for elution. Following chromatography, 4.5 mg of 2r and 44.6 mg of 3r were obtained, and the yields were 5% and 44%, respectively.

Reference： [1]Chen, Ying-Zhe; Ni, Ching-Wen; Teng, Fu-Lin; Ding, Yi-Shun; Lee, Tunng-Hsien; Ho, Jinn-Hsuan [Tetrahedron, 2014, vol. 70, # 9, p. 1748 - 1762]

70
[ 1485-07-0 ]
2-((trifluoromethyl)thio)benzo[d]isothiazol-3(2H)-one 1,1-dioxide [ No CAS ]
((2-(naphthalen-2-yl)ethoxy)(trifluoromethyl)sulfane) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine In dichloromethane at 20℃; for 0.0833333h;
95%	With triethylamine In dichloromethane at 20℃; for 0.0833333h;	1 Example 1 50mL egg-shaped flask was added N - saccharin trifluoromethylthio group 1 (110mg, 0.39mmol), naphthyl ethyl alcohol (52.0mg, 0.3mmol), triethylamine under 96μL (0.69mmol), methylene chloride (6mL), room temperature The reaction 5min.After completion of the reaction, the reaction solution rapidly by about 6 millimeters silica gel column, the column with the amount of methylene chloride and washed twice, and the combined organic liquid, spin dry to give trifluoromethyl - (2 naphthaleneethanyl) thio peroxide (78mg, 95% isolated yield).Purity by NMR identified more than 95%.Trifluoromethyl - (2-naphthylethyl) thio peroxy ((2- (naphthalen-2-YL) Ethoxy) (trifluoromethyl) sulfane):

Reference： [1]Xu, Chunfa; Ma, Bingqing; Shen, Qilong [Angewandte Chemie - International Edition, 2014, vol. 53, # 35, p. 9316 - 9320,5][Angew. Chem., 2014, vol. 126, # 35, p. 9470 - 9474,5][Angewandte Chemie, 2014, vol. 126, # 35, p. 9470 - 9474,5]
[2]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN104945298, 2016, B Location in patent: Paragraph 0068; 0069; 0070; 0071

71
[ 1485-07-0 ]
(S)-ethyl 2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-5-(4-hydroxyphenyl)-2,6-dimethylpyridin-3-yl)acetate [ No CAS ]
(S)-2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethyl-5-(4-(2-(naphthalen-2-yl)ethoxy)phenyl)pyridin-3-yl)acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10.64%	Stage #1: naphthalen-2-ethanol; (S)-ethyl 2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-5-(4-hydroxyphenyl)-2,6-dimethylpyridin-3-yl)acetate With diethylazodicarboxylate In tetrahydrofuran at 20℃; for 18h; Stage #2: With methanol; sodium hydroxide at 75℃; for 16h;	30 Example 30 j0253]Example 3010254] To a stirred solution of (5)-ethyl 2-(tert-butoxy)-2- (4-(4,4-dimethylpiperidin- 1 -yl)-5-(4-hydroxyphenyl)-2,6-dimethylpyridin-3-yl)acetate (20 mg, 0.043 mmol), 2-(naph- thalen-2-yl)ethanol (36.8 mg, 0.213 mmol) and Ph3P-resin (55.8 mg, 0.213 mmol) in THF (2 mE) was added DEAD (0.014 mE, 0.085 mmol) at it. Afier 18 h, mixture was filtered to remove polymer, concentrated and treated with iN NaOH (0.854 mE, 0.854 mmol) in MeOH (1 mE) at 75° C. for 16 h. Mixture was then cooled and purified by prep-HPEC to afford (S)-2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-i -yl)-2,6-dimethyl-5-(4-(2-(naphthalen-2-yl)ethoxy)phenyl)pyridin- 3-yl)acetic acid (2.7 mg, 4.54 tmol, 10.64% yield). ‘H NMR (500 MHz, DMSO-d5) ö 7.92-7.80 (m, 4H), 7.57-7.46 (m, 3H), 7.21 (d, J=8.4 Hz, 1H), 7.10-6.93 (m, 3H), 5.83 (s, 1H),4.45-4.26 (m, 2H), 3.45-3.24 (m, 3H), 2.80 (t, J=ii.2 Hz, 1H), 2.43 (s, 3H), 2.17 (bt s., 1H), 2.05 (s, 3H), 1.99-1.91 (m, 1H), 1.48 (bt s., 1H), 1.37-1.27 (m, 1H), 1.17 (d, J=13.9 Hz, 1H), 1.12 (s, 9H), 1.02 (d, J=ii.7 Hz, 1H), 0.84 (s, 3H), 0.60 (s, 3H). ECMS (M+H)=595.5.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US2015/232463, 2015, A1 Location in patent: Paragraph 0253; 0254

72
[ 1485-07-0 ]
[ 106-96-7 ]
2-(2-(prop-2-yn-1-yloxy)ethyl)naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: naphthalen-2-ethanol With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: propargyl bromide In tetrahydrofuran

Reference： [1]Xu, Zhou; Chen, Hongyi; Wang, Zhixun; Ying, Anguo; Zhang, Liming [Journal of the American Chemical Society, 2016, vol. 138, # 17, p. 5515 - 5518]

73
[ 1485-07-0 ]
[ 124-63-0 ]
C₁₃H₁₄O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at 20℃; for 3h; Cooling with ice;	2-Naphthalene ethanol (203a) a (1.00 g) was dissolved in CH2Cl2 (4mL), triethylamine under ice cooling(705 mg), was added MsCl (789 mg). After stirring the reaction mixture at room temperature for 3 hours, the reaction was quenched with saturated sodium hydrogen carbonate aqueous solution (30 mL).The reaction solution was extracted with CHCl3 (50 mL), the organic layer was washed with water (50 mL), washed with saturated brine (50 mL), and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reducedpressure, to give the corresponding mesylate. Then 0.5M sodium azide DMSO solution (13.9 mL) was added to the mesylate,followed by stirring for 2 hours at 80 ° C. Water (30 mL) was added to the reaction solution, the reaction mixture wasextracted with ethyl acetate (100 mL). The organic layer was washed with water (100 mL), washed with saturated brine (100mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified bysilica gel flash column chromatography (developing solvent nhexane:ethyl acetate = 50: 1) to give crude crystals (906 mg,79% yield, 2 Steps) was obtained. The crude crystals were recrystallized from AcOEt / nhexan,to give the title compound(319 mg) as a white solid.

Reference： [1]Current Patent Assignee: NAGOYA CITY UNIVERSITY - JP5725475, 2015, B2 Location in patent: Paragraph 0131; 0132

74
[ 603-76-9 ]
[ 1485-07-0 ]
1-(1-methyl-1H-indol-3-yl)-2-(naphthalen-2-yl)ethane-1,2-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94.8%	With 1-methyl-piperazine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; zinc trifluoromethanesulfonate In 1-methyl-pyrrolidin-2-one at 120℃; for 4h; Inert atmosphere;	3 In an appropriate amount of N-methylpyrrolidone,100 mmol of the compound of formula (II) 2- (naphthalen-2-yl) ethanol was added,300 mmol of the compound of formula (III) 1-methyl-1H-indole,5 mmol of zinc trifluoromethanesulfonate,300 mmol of TEMPO and 60 mmol of N-methylpiperazine,Then purged with nitrogen for 2-3 times; the temperature was raised to 120 ° C and the reaction was stirred at that temperature for 4 hours,During the period has been through the nitrogen for bubbling,To ensure that the reaction system is always reacted in a nitrogen atmosphere,Until the end of the reaction.After completion of the reaction, the reaction system was allowed to cool to room temperature and then deionized water was added.The combined solution was extracted with ethyl acetate and chromatographed. The upper organic phase was taken and the mass percentage15% aqueous Na2S2O3 solution, dried over anhydrous sodium sulfate and then evaporated under reduced pressure to dry the residueA mixture of 200-400 mesh silica gel column chromatography (using a mixture of acetone and absolute ethanol as an eluentThe volume ratio of acetone to absolute ethanol was 6: 1) to give the title compound 1- (1-methyl-1H-indol-3-yl)2- (naphthalen-2-yl) ethane-1,2-dione in a yield of 94.8%

Reference： [1]Current Patent Assignee: Shenzhen Poly-tech Electronic Co., Ltd; Zheng, Chao - CN104557663, 2016, B Location in patent: Paragraph 0046-0049

75
[ 1485-07-0 ]
[ 530-62-1 ]
C₁₃H₁₃NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: naphthalen-2-ethanol; 1,1'-carbonyldiimidazole In toluene at 60℃; Stage #2: With hydroxylamine In water; toluene at 20℃;
	Stage #1: naphthalen-2-ethanol; 1,1'-carbonyldiimidazole In acetonitrile at 20℃; for 2h; Inert atmosphere; Stage #2: With 1H-imidazole; hydroxylamine hydrochloride In acetonitrile at 20℃; Inert atmosphere;

Reference： [1]Lebel, Hélène; Mamani Laparra, Laura; Khalifa, Maroua; Trudel, Carl; Audubert, Clément; Szponarski, Mathieu; Dicaire Leduc, Cédric; Azek, Emna; Ernzerhof, Matthias [Organic and Biomolecular Chemistry, 2017, vol. 15, # 19, p. 4144 - 4158]
[2]Chen, Shuming; Hong, Yubiao; Houk, K. N.; Ivlev, Sergei; Meggers, Eric; Tan, Yuqi; Zhou, Zijun [Angewandte Chemie - International Edition, 2020, vol. 59, # 48, p. 21706 - 21710][Angew. Chem., 2020, vol. 132, # 48, p. 21890 - 21894,5]

76
[ 1485-07-0 ]
(E)-2,2'-(prop-1-ene-1,3-diyl)dinaphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With tris(triphenylphosphine)ruthenium(II) chloride; 1,3-bis-(diphenylphosphino)propane; sodium t-butanolate In toluene at 111℃; for 24h; Inert atmosphere;
76%	With [Mn(HN(C₂H₄PⁱPr₂)₂)(CO)₂Br]; sodium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene at 145℃; for 16h; Schlenk technique; Inert atmosphere;

Reference： [1]Manojveer, Seetharaman; Forrest, Sebastian J. K.; Johnson, Magnus T. [Chemistry - A European Journal, 2018, vol. 24, # 4, p. 803 - 807]
[2]Wang, Yujie; Shao, Zhihui; Zhang, Kun; Liu, Qiang [Angewandte Chemie - International Edition, 2018, vol. 57, # 46, p. 15143 - 15147][Angew. Chem., 2018, vol. 130, p. 15363 - 15367,5]

77
[ 1485-07-0 ]
1-(2-nitrophenyl)ethyl (2-nitrophenyl)sulfonylcarbamate [ No CAS ]
1-(2-nitrophenyl)ethyl (2-nitrophenyl)sulfonyl(octyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With triphenylphosphine; diethylazodicarboxylate In toluene; benzene for 16h;	Typical procedure for N-alkylation of NPEC-NHNs (3) by Mitsunobu reaction (Table 1, entry 2): 1-(2-nitrophenyl)ethyl (2-(naphthalen-2-yl)ethyl)((2-nitrophenyl)sulfonyl)carbamate (4b) To a stirred solution of NPEC-NHNs (3, 30.8 mg, 0.0760 mmol) inbenzene (0.500 mL) at rt were added 2-naphthaleneethanol (27.0 mg,0.150 mmol), triphenylphosphine (40.0 mg, 0.150 mmol), and a solutionof diethyl azodicarboxylate in toluene (2.2 M, 0.070 mL, 0.15 mmol). After 16 h, the reaction mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography (60N, 1.6g, MeOH/CHCl3 = 1:19) to give naphthalenylethylamine 4b (41.0 mg,95%) as a pale yellow oil: IR (ATR) 3057, 1732, 1542, 1443, 1365,1264, 1200, 1171, 1139, 1057, 854 cm-1; 1H NMR (400 MHz, CDCl3) δ 8.26(d, J = 7.8 Hz, 1H), 7.91 (d, J = 7.6 Hz, 1H), 7.82-7.75 (m, 3H),7.73 (d, J = 4.2 Hz, 2H), 7.71-7.63 (m, 2H), 7.51-7.33 (m, 5H), 7.27(d, J = 7.5 Hz, 1H), 6.20 (q, J = 6.4 Hz, 1H), 4.16 (dt, J = 7.4,3.3 Hz, 2H), 3.20 (t, J = 7.6 Hz, 2H), 1.44 (d, J = 6.4 Hz, 3H); 13CNMR (100 MHz, CDCl3) δ 150.7, 147.8, 147.1, 136.7, 135.1, 134.6,133.9, 133.7, 133.6, 132.9, 132.4, 131.8, 128.7, 128.3, 127.7, 127.7,127.6, 127.4, 126.7, 126.1, 125.6, 124.6, 124.5, 72.3, 49.3, 36.9,21.7.

Reference： [1]Miyahara, Masayoshi; Shiozaki, Hiroki; Tukada, Hideyuki; Ishikawa, Yuichi; Oikawa, Masato [Tetrahedron Letters, 2018, p. 4259 - 4262]

78
[ 5402-55-1 ]
[ 1485-07-0 ]
2-(3-(naphthalen-2-yl)propyl)thiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: 2-thiophenethanol; naphthalen-2-ethanol With [Mn(HN(C₂H₄PⁱPr₂)₂)(CO)₂Br]; sodium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene at 145℃; for 16h; Schlenk technique; Inert atmosphere; Stage #2: With hydrogen In methanol at 50℃; for 16h; Autoclave;

Reference： [1]Wang, Yujie; Shao, Zhihui; Zhang, Kun; Liu, Qiang [Angewandte Chemie - International Edition, 2018, vol. 57, # 46, p. 15143 - 15147][Angew. Chem., 2018, vol. 130, p. 15363 - 15367,5]

79
[ 1485-07-0 ]
[ 100-51-6 ]
2-(naphthalen-2-yl)-3-phenylpropan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With tris(triphenylphosphine)ruthenium(II) chloride; potassium <i>tert</i>-butylate In toluene at 120℃; for 24h;

Reference： [1]Manojveer, Seetharaman; Salahi, Saleh; Wendt, Ola F.; Johnson, Magnus T. [Journal of Organic Chemistry, 2018, vol. 83, # 18, p. 10864 - 10870]

80
[ 1485-07-0 ]
[ 124-63-0 ]
[ 102072-41-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at 20℃; for 3h; Cooling with ice;	2-Naphthalene ethanol (203a) a (1.00 g) was dissolved in CH2Cl2 (4mL), triethylamine under ice cooling(705 mg), was added MsCl (789 mg). After stirring the reaction mixture at room temperature for 3 hours, the reaction was quenched with saturated sodium hydrogen carbonate aqueous solution (30 mL).The reaction solution was extracted with CHCl3 (50 mL), the organic layer was washed with water (50 mL), washed with saturated brine (50 mL), and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reducedpressure, to give the corresponding mesylate. Then 0.5M sodium azide DMSO solution (13.9 mL) was added to the mesylate,followed by stirring for 2 hours at 80 ° C. Water (30 mL) was added to the reaction solution, the reaction mixture wasextracted with ethyl acetate (100 mL). The organic layer was washed with water (100 mL), washed with saturated brine (100mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified bysilica gel flash column chromatography (developing solvent nhexane:ethyl acetate = 50: 1) to give crude crystals (906 mg,79% yield, 2 Steps) was obtained. The crude crystals were recrystallized from AcOEt / nhexan,to give the title compound(319 mg) as a white solid.

Reference： [1]Current Patent Assignee: NAGOYA CITY UNIVERSITY - JP5725475, 2015, B2 Location in patent: Paragraph 0131; 0132

81
[ 67-56-1 ]
[ 1485-07-0 ]
[ 38964-52-2 ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium <i>tert</i>-butylate; C₃₇H₃₆Cl₂NPRuS₂ at 135℃; for 36h; Sealed tube; Inert atmosphere; Green chemistry;
	With trimethylamine-N-oxide; (1,4-dimethyl-5,7-diphenyl-1,2,3,4-tetrahydro-6H-cyclopenta[b]pyrazin-6-one) irontricarbonyl complex3; sodium hydroxide at 130℃; for 24h;

Reference： [1]Biswas, Nandita; Srimani, Dipankar [Journal of Organic Chemistry, 2021, vol. 86, # 15, p. 10544 - 10554]
[2]Polidano, Kurt; Williams, Jonathan M. J.; Morrill, Louis C. [ACS Catalysis, 2019, vol. 9, # 9, p. 8575 - 8580]

82
[ 540-88-5 ]
[ 1485-07-0 ]
[ 1612215-51-6 ]

Yield	Reaction Conditions	Operation in experiment
55 %Chromat.	With H-USY zeolite CBV-720 In toluene at 75℃; for 4h;	Zeolite-Catalyzed tert-Butylation Of Alcohols General procedure: Alcohol 7a-s (0.4 mmol) was weighed in a test tube, then the correspondingamount of tert-butyl acetate (8; 68 L, 0.5 mmol) and toluene(0.5 mL) were added. A 20 L sample was taken as the zero-timesample and diluted in a vial with EtOAc (1 mL) to be analyzed usingGC, with n-dodecane (22 L, 0.1 mmol) as an internal standard. Themixture was then added to a vial containing 5 mol% H+ of the zeolite(50 wt% for 7a) and a magnetic stirrer. The vial was placed in a siliconebath at 75 °C. The reaction was typically run for 240 min and 20L samples were taken throughout the reaction, and each was placedin a vial with EtOAc (1 mL). Each sample was then filtered to remove any solid catalyst in the sample, and then analyzed by GC with n-dodecane(22 mL, 0.1 mmol) as an external standard. Most of the productsare reported and characterized in the literature: 9a,21b 9g,21c9h,21d 9i,21e 9k-l,n,21f 9m,21g 9o,21h 9p,s,21i 9q,21j 9r.21k

Reference： [1]Blake, Finn; Leyva-Pérez, Antonio; Sanz-Navarro, Sergio; Tejeda-Serrano, María [Synthesis, 2020, vol. 52, # 14, p. 2031 - 2037]

83
[ 1485-07-0 ]
[ 2638-22-4 ]
2-(naphthalen-2-yl)ethyl 2,6-dimethoxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With dmap; triethylamine In dichloromethane at 20℃; for 24h;

Reference： [1]Mayr, Stefanie; Marin-Luna, Marta; Zipse, Hendrik [Journal of Organic Chemistry, 2021, vol. 86, # 4, p. 3456 - 3489]

84
[ 1485-07-0 ]
2-methoxy-6-phenylbenzoic anhydride [ No CAS ]
2-(naphthalen-2-yl)ethyl 2-methoxy-6-phenylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With dmap; triethylamine In dichloromethane at 20℃; for 24h;

Reference： [1]Mayr, Stefanie; Marin-Luna, Marta; Zipse, Hendrik [Journal of Organic Chemistry, 2021, vol. 86, # 4, p. 3456 - 3489]

85
[ 1485-07-0 ]
[ 73368-14-6 ]
2-(naphthalen-2-yl)ethyl 2,6-dimethylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With dmap; triethylamine In dichloromethane at 20℃; for 24h;

Reference： [1]Mayr, Stefanie; Marin-Luna, Marta; Zipse, Hendrik [Journal of Organic Chemistry, 2021, vol. 86, # 4, p. 3456 - 3489]

86
[ 1485-07-0 ]
2-methyl-6-phenylbenzoic anhydride [ No CAS ]
2-(naphthalen-2-yl)ethyl 2-methyl-6-phenylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With dmap; triethylamine In dichloromethane at 20℃; for 24h;

Reference： [1]Mayr, Stefanie; Marin-Luna, Marta; Zipse, Hendrik [Journal of Organic Chemistry, 2021, vol. 86, # 4, p. 3456 - 3489]

87
[ 1485-07-0 ]
[ 434935-69-0 ]
2-(naphthalen-2-yl)ethyl 2-methyl-6-nitrobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With dmap; triethylamine In dichloromethane at 20℃; for 24h;
65%	With dmap; triethylamine at 20℃; for 24h;

Reference： [1]Mayr, Stefanie; Marin-Luna, Marta; Zipse, Hendrik [Journal of Organic Chemistry, 2021, vol. 86, # 4, p. 3456 - 3489]
[2]Mayr, Stefanie; Zipse, Hendrik [European Journal of Organic Chemistry, 2022]

88
[ 64985-86-0 ]
[ 1485-07-0 ]
2-(naphthalen-2-yl)ethyl 1-naphthoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With dmap; triethylamine In dichloromethane at 20℃; for 24h;

Reference： [1]Mayr, Stefanie; Marin-Luna, Marta; Zipse, Hendrik [Journal of Organic Chemistry, 2021, vol. 86, # 4, p. 3456 - 3489]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	1485-07-0	MDL No. :	MFCD00004128
Formula :	C₁₂H₁₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VCZANYLMPFRUHG-UHFFFAOYSA-N
M.W :	172.22	Pubchem ID :	73877
Synonyms :

Num. heavy atoms :	13
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.17
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	54.88
TPSA :	20.23 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.11 cm/s

Log Po/w (iLOGP) :	2.09
Log Po/w (XLOGP3) :	3.16
Log Po/w (WLOGP) :	2.37
Log Po/w (MLOGP) :	2.85
Log Po/w (SILICOS-IT) :	3.18
Consensus Log Po/w :	2.73

[ CAS No. 1485-07-0 ] {[proInfo.proName]}

Quality Control of [ 1485-07-0 ]

Related Doc. of [ 1485-07-0 ]

Product Details of [ 1485-07-0 ]

Calculated chemistry of [ 1485-07-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1485-07-0 ]

Application In Synthesis of [ 1485-07-0 ]

[ 1485-07-0 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Log S (ESOL) :	-3.34
Solubility :	0.0795 mg/ml ; 0.000462 mol/l
Class :	Soluble
Log S (Ali) :	-3.26
Solubility :	0.0957 mg/ml ; 0.000556 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.3
Solubility :	0.00859 mg/ml ; 0.0000499 mol/l
Class :	Moderately soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P302+P352-P304+P340-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling