Name: 30012-51-2|Methyl 2-(6-methoxynaphthalen-2-yl)propanoate|95%
Brand: Ambeed
SKU: A771664
Price: 31.0 USD
Availability: InStock
Rating: 91 (26 reviews)

1
[ 908094-01-9 ]
[ 23981-80-8 ]
[ 30012-51-2 ]

Yield	Reaction Conditions	Operation in experiment
65%	In diethyl ether at 0℃; for 1h;

Reference： [1]Hiyama; Inoue [Synthesis, 1986, vol. NO. 8, # 8, p. 689 - 691]

2
[ 67-56-1 ]
[ 23981-80-8 ]
[ 30012-51-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sulfuric acid
100%		2 Example 2; Methyl (RS)-2-(6-methoxynaphthalen-2-yl)propanoate; To a solution of (fiS)-2-(6-methoxynaphthalen-2-yl)piOpanoic acid (14.25 g, 62.8 mmol) in methanol (450 ml_) was added 70 drops of concentrated H2SO4 and the reaction mixture was stirred for overnight before it was diluted with CH2CI2 (approx. 1 L), washed with aqueous saturated NaHCO3 and dried over Na2SO4. Solvent evaporation gave the title methyl ester quantitatively. 1H NMR (400 MHz, CDCI3): δ = 7.62 (s, 1 H), 7.57 (d, 1 H, J = 8.5 Hz), 7.48-7.45 (m, 2H), 7.18 (d, 1 H, J = 2.6 Hz), 6.89 (d, 1 H, J = 2.4 Hz), 3.71 (q, 1 H, J = 7.1 Hz), 3.36 (s, 3H), 3.28 (s, 3H), 1.52 (d, 3H, J = 7.1 Hz).
100%	With sulfuric acid for 6h; Reflux;	3.1 In a 250 mL flask connected to a reflux condenser there were added 0.7 g (3 mmol) of naproxen, 50 mL of methanol and 2 drops of concentrated sulfuric acid. The reaction is kept under reflux and stirring for 6 hours until thin layer chromatography indicated the completion of the reaction (Mobile phase: 90% dichloromethane; 10% methanol).The product was obtained by removing the solvent at reduced pressure to provide 0.74 g of an orange color solid with melting range between 88°-94° C. (C15H16O3, MW=244.11, yield: 100%).The NMR H1 spectrum (400 MHz, DMSOd) was as follows: δ 1.47 (d; 3H); 3.59 (s; 3H); 3.86 (s; 3H); 3.94 (q; 1H); 7.15 (dd; 1H; Jorto=8.7 Hz and Jmeta=2.56 Hz); 7.29 (d; 1H; Jmeta=2.56 Hz); 7.38 (dd; 1H; Jorto=8.53 Hz and Jmeta=1.87 Hz); 7.72 (d; 1H); 7.79 (Jorto=8.87 Hz; 2H) ppm.The IR spectrum (KBr pellet) was as follows: ν 2976 (C-H, CH2 and CH3) ν 1739.7 (COester) δ 1604, 1450 (C-Haromatic); V 1267 (C-O) cm-1.

98%	Stage #1: methanol; 2-(6-methoxy-naphthalen-2-yl)-propionic acid With dmap In dichloromethane at 0℃; for 0.0833333h; Stage #2: With dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 3.08333h;
96%	With sulfuric acid In chloroform at 70℃; for 3h; Dean-Stark;
96%	With sulfuric acid; magnesium(II) sulfate In dichloromethane at 20℃; for 24h;
95%	With sulfuric acid at 20℃; for 2h;
92%	With sulfuric acid at 60 - 70℃; for 1.16667h;
73%	With thionyl chloride for 2h; Heating;
	With sulfuric acid for 6h; Heating;
	With thionyl chloride at 0 - 20℃;
	With sulfuric acid Heating;
	With sulfuric acid for 6h; Reflux;
	With sulfuric acid at 55℃; for 18h;
	With sulfuric acid for 2h; Reflux;
	With sulfuric acid for 3h; Reflux;
	With sulfuryl dichloride Reflux;
	With sulfuric acid for 14h; Reflux;
17.2 mg	With diazomethyl-trimethyl-silane In toluene at 20℃; for 1h;

Reference： [1]Noorduin, Wim L.; Kaptein, Bernard; Meekes, Hugo; Enckevort, Willem J. P. van; Kellogg, Richard M.; Vlieg, Elias [Angewandte Chemie - International Edition, 2009, vol. 48, p. 4581 - 4583][Angew. Chem., Int. Ed., 2009, vol. 121, p. 4651 - 4653]
[2]Current Patent Assignee: KONINKLIJKE DSM N.V. - WO2010/89343, 2010, A1 Location in patent: Page/Page column 8-9
[3]Current Patent Assignee: UNIVERSIDAE ESTADUAL PAULISTA - US2012/115817, 2012, A1 Location in patent: Page/Page column 43
[4]Liang, Yu-Feng; Jiao, Ning [Angewandte Chemie - International Edition, 2014, vol. 53, # 2, p. 548 - 552][Angew. Chem., 2014, vol. 53, # 2, p. 558 - 562,5]
[5]Gilani, Saeedeh L.; Najafpour, Ghasem D.; Heydarzadeh, Hamid D.; Moghadamnia, Aliakbar [Chirality, 2017, vol. 29, # 6, p. 304 - 314]
[6]Xie, Qiqiang; Zhu, Ziyue; Li, Lingchun; Ni, Chuanfa; Hu, Jinbo [Angewandte Chemie - International Edition, 2019, vol. 58, # 19, p. 6405 - 6410][Angew. Chem., 2019, vol. 131, # 19, p. 6471 - 6476,6]
[7]Muñoz-Muñiz, Omar; Juaristi, Eusebio [Tetrahedron Letters, 2003, vol. 44, # 10, p. 2023 - 2026]
[8]Koul, Surrinder; Parshad, Rajinder; Taneja, Subhash C.; Qazi, Ghulam N. [Tetrahedron Asymmetry, 2003, vol. 14, # 16, p. 2459 - 2465]
[9]Giorno; D'Amore; Drioli; Cassano; Picci [Journal of Catalysis, 2007, vol. 247, # 2, p. 194 - 200]
[10]Ghislandi; La Manna; Azzolina; et al. [Farmaco, Edizione Scientifica, 1982, vol. 37, # 2, p. 81 - 93]
[11]Fujisawa, Hidehito; Fujiwara, Tomoya; Takeuchi, Yoshio; Omata, Kenji [Chemical and Pharmaceutical Bulletin, 2005, vol. 53, # 5, p. 524 - 528]
[12]Stock, Nicholas; Munoz, Benito; Wrigley, Jonathan D.J.; Shearman, Mark S.; Beher, Dirk; Peachey, James; Williamson, Toni L.; Bain, Gretchen; Chen, Weichao; Jiang, Xiaohui; St-Jacques, Rene; Prasit, Peppi [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 8, p. 2219 - 2223]
[13]Location in patent: experimental part Parcha, Versha; Kaur, Jaswinder; Gupta, Vinay; Anroop [Journal of the Indian Chemical Society, 2008, vol. 85, # 3, p. 321 - 325]
[14]Wang, Pei-Yun; Chen, Ying-Ju; Wu, An-Chi; Lin, Yi-Sheng; Kao, Min-Fang; Chen, Jin-Ru; Ciou, Jyun-Fen; Tsai, Shau-Wei [Advanced Synthesis and Catalysis, 2009, vol. 351, # 14-15, p. 2333 - 2341]
[15]Windsor, Matthew A.; Hermanson, Daniel J.; Kingsley, Philip J.; Xu, Shu; Crews, Brenda C.; Ho, Winnie; Keenan, Catherine M.; Banerjee, Surajit; Sharkey, Keith A.; Marnett, Lawrence J. [ACS Medicinal Chemistry Letters, 2012, vol. 3, # 9, p. 759 - 763]
[16]Aydin, Sevil; Kaushik-Basu, Neerja; Oezbas-Turan, Suna; Akbuga, Juelide; Tiber, Pinar Mega; Orun, Oya; Gurukumar; Basu, Amartya; Kuecuekguezel, S. Gueniz [Letters in drug design and discovery, 2014, vol. 11, # 2, p. 121 - 131]
[17]Li, Zhiyou; Wu, Lamei; Zhang, Tao; Huang, Zhengxi; Qiu, Guofu; Zhou, Zhongqiang; Jin, Longfei [Dalton Transactions, 2014, vol. 43, # 20, p. 7554 - 7560]
[18]Abrams, M. Leigh; Buser, Jonas Y.; Calvin, Joel R.; Johnson, Martin D.; Jones, Bradley R.; Lambertus, Gordon; Landis, Clark R.; Martinelli, Joseph R.; May, Scott A.; McFarland, Adam D.; Stout, James R. [Organic Process Research and Development, 2016, vol. 20, # 5, p. 901 - 910]
[19]Jiang, Yi-Qian; Lan, Yu; Li, Shi-Jun; Li, Wen-Duo; Li, Yan-Lin; Wu, Yang; Xia, Ji-Bao [Journal of the American Chemical Society, 2021]

3
[ 67-56-1 ]
S(+)-2-bromo-1-(6-methoxy-2-naphthyl)-propan-1-one [ No CAS ]
[ 30012-51-2 ]
[ 76145-97-6 ]

Yield	Reaction Conditions	Operation in experiment
	With zinc dibromide at 115℃; for 4h;
	With boron trifluoride; silver carbonate at 15℃; for 20h;

Reference： [1]Giordano, Claudio; Castaldi, Graziano; Uggeri, Fulvio; Gurzoni, Francesco [Synthesis, 1985, # 4, p. 436 - 437]
[2]Giordano, Claudio; Castaldi, Graziano; Casagrande, Francesco; Abis, Luigi [Tetrahedron Letters, 1982, vol. 23, # 13, p. 1385 - 1386]

4
[ 17639-93-9 ]
[ 5111-65-9 ]
[ 30012-51-2 ]

Yield	Reaction Conditions	Operation in experiment
55%	With (2,2'-bipyridine)nickel(II) dibromide; tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide at 70℃; i = 250 mA, nickel-sponge cathode;
45%	With [2,2]bipyridinyl; tetrabutylammomium bromide; nickel dibromide In N,N-dimethyl-formamide for 5h; electrochemical process;

Reference： [1]Durandetti, Muriel; Nedelec, Jean-Yves; Perichon, Jacques [Journal of Organic Chemistry, 1996, vol. 61, # 5, p. 1748 - 1755]
[2]Conan, Annie; Sibille, Soline; d'Incan, Esther; Perichon, Jacques [Journal of the Chemical Society. Chemical communications, 1990, # l, p. 48 - 49]

5
[ 30012-51-2 ]
[ 23981-80-8 ]

Yield	Reaction Conditions	Operation in experiment
63%	With formic acid; sulfuric acid; In water; ethyl acetate; toluene;	REFERENCE EXAMPLE 2 150 mg of methyl d-alpha-(6-methoxynaphth-2-yl)propionate ([alpha]D20 =+77.4) was dissolved in a mixed solution of 3.0 g of formic acid, 0.3 g of water and 0.3 g of concentrated sulfuric acid, and the solution was heated at 40 C. for 6 hours. Water was added thereto, and the solution was extracted with a mixture of toluene and ethylacetate. The organic extracts were combined, and extracted three times with an aqueous sodium hydroxide solution. The organic layer was concentrated, and 60.1 mg of the starting material was thereby recovered. The alkaline layer was acidified with 10% hydrochloric acid, extracted with ethyl acetate and concentrated under reduced pressure, whereupon 89.2 mg of d-alpha-(6-methoxynaphth-2-yl)propionic acid was obtained as colourless crystals. The yield was 63%. The optical rotation was [alpha]D20 =+58.9 and the optical purity was 88%. m.p.; 156 to 157 C. NMR (CDCl3) delta; 1.57 (3H, d, 7 Hz), 3.83 (1H, q, 7 Hz), 3.86 (3H, s), 6.9-8.05 (6H, m), 8.0 (1H, broad s) IR (KBr); 2930, 1690, 1595, 1380, 1260, 1223, 1027, 920, 853, 820, 673, 480 cm-1 MS(m/e); 230 (93, M+), 185 (100)
	With hydrogenchloride; sodium hydroxide; In methanol;	EXAMPLE 19 To a mixture of 20 g. of sodium hydroxide and 400 ml. of methanol are added 24.5 g. of methyl 6methoxy-2-naphthyl-alpha -methylacetate. The resulting reaction mixture is heated to 60C for five hours. The cooled mixture is neutralized by the addition of aqueous 1N hydrochloric acid and extracted with methylene chloride. The extracts are combined, washed with water to neutrality, dried over sodium sulfate, filtered, and evaporated to give 6-methoxy-2naphthyl-alpha-methylacetic acid. Similarly, the other 2-naphthylacetic acid ester derivatives prepared by means of the procedures described in the other examples herein are hydrolyzed to the corresponding 2-naphthylacetic acid derivatives.

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1982,p. 2575 - 2582
[2]Journal of the Chemical Society. Perkin transactions I,1994,p. 1323 - 1328
[3]Organic Letters,2019,vol. 21,p. 3299 - 3303
[4]Patent: US4417070,1983,A
[5]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1990,vol. 29,p. 304 - 309
[6]Synthesis,1985,p. 436 - 437
[7]Journal of Organic Chemistry,1983,vol. 48,p. 4658 - 4661
[8]Tetrahedron Letters,1982,vol. 23,p. 1385 - 1386
[9]Tetrahedron,1994,vol. 50,p. 1243 - 1260
[10]Bioorganic chemistry,2002,vol. 30,p. 276 - 284
[11]Patent: US3978116,1976,A
[12]Organic Syntheses,1999,vol. 76,p. 169 - 169

6
[ 30012-51-2 ]
[ 22204-53-1 ]

Yield	Reaction Conditions	Operation in experiment
	With mercaptoethyl alcohol; Polyvinyl alcohol at 22℃; for 216h; Candida cylindracea lipase, 0.2 M potassium phosphate buffer, pH=8.0; Yield given;
40 % Turnov.	With sodium hydroxide; Tween-80 In water at 40℃; for 3.25h; titrisol buffer pH 8, carboxylesterase NP;
	With water at 40℃; for 20h; Candida rugosa lipase, pH 5; Yield given;

	With phosphate buffer In 2,2,4-trimethylpentane at 30℃;
	Multi-step reaction with 4 steps 1: sodium borohydride / methanol / 4 h 2: triethylamine; DMAP / CH₂Cl₂ / 1 h / 20 °C 3: pig pancreatic lipase; phosphate buffer / acetone / pH 8.0 4: pyridinium dichromate / dimethylformamide / 72 h
> 98 % ee	With Candida rugosa lipase immobilized on calix[4]arene-1 carboxylic acid-grafted magnetic nanoparticles at 35℃; for 24h;
	With Candida rugosa lipase immobilized on activated by glutaraldehyde chitosan beads In 2-ethoxy-ethanol; aq. phosphate buffer; 2,2,4-trimethylpentane at 35℃; for 24h; Enzymatic reaction; enantioselective reaction;

Reference： [1]Gu; Chen; Sih [Tetrahedron Letters, 1986, vol. 27, # 16, p. 1763 - 1766]
[2]Smeets, J. W. H.; Kieboom, A. P. G. [Recueil des Travaux Chimiques des Pays-Bas, 1992, vol. 111, # 11, p. 490 - 495]
[3]Lalonde, Jim J.; Govardhan, Chandrika; Khalaf, Nazer; Martinez, Aldo G.; Visuri, Kalevi; Margolin, Alexey L. [Journal of the American Chemical Society, 1995, vol. 117, # 26, p. 6845 - 6852]
[4]Giorno; D'Amore; Drioli; Cassano; Picci [Journal of Catalysis, 2007, vol. 247, # 2, p. 194 - 200]
[5]Basak, Amit; Nag, Ahindra; Bhattacharya, Gautam; Mandal, Subrata; Nag, Sikha [Tetrahedron Asymmetry, 2000, vol. 11, # 11, p. 2403 - 2407]
[6]Akceylan, Ezgi; Sahin, Ozlem; Yilmaz, Mustafa [Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2014, vol. 79, # 1-2, p. 113 - 123]
[7]Gilani, Saeedeh L.; Najafpour, Ghasem D.; Heydarzadeh, Hamid D.; Moghadamnia, Aliakbar [Chirality, 2017, vol. 29, # 6, p. 304 - 314]

7
[ 30012-51-2 ]
[ 22204-53-1 ]
[ 23979-41-1 ]

Yield	Reaction Conditions	Operation in experiment
	With Thermotoga maritima esterase Tm1160; In aq. acetate buffer; at 70℃;pH 5.5;Enzymatic reaction;	General procedure: Enzymatic reactions were carried out at 70 C in 1 ml of a reaction mixture containing the purified enzyme (0.235 mg) and 25 mg of racemic ketoprofen ethyl ester dissolved in 50 mM sodium acetate buffer (pH 5.5). The reaction mixture was stirred at 200 rpm. The resulting solution was analyzed by HPLC using the chiral column (25 cm × 4.6 cm, Daical Chemical Industries, Tokyo, Japan). Samples were eluted with n-hexane:2-propanol:acetic acid (90:10:0.5, v/v/v) at a flow rate of 1.0 mL/min and detected at 254 nm. The retention times of racemic ketoprofen ethyl ester, R-ketoprofen, and S-ketoprofen were detected at 5.4, 14.8 and 18.2 min, respectively. The enantioselectivity of the enzyme was calculated with E = ln[1 - c(1 + eep)]/ln[1 - c(1 - eep)], where c and eep represent the degree of conversion and the enantiomeric excess of product, respectively [34].

Reference： [1]Agricultural and Biological Chemistry,1981,vol. 45,p. 1389 - 1392
[2]Journal of Catalysis,2007,vol. 247,p. 194 - 200
[3]Journal of Molecular Catalysis B: Enzymatic,2013,vol. 85-86,p. 23 - 30

8
[ 30012-51-2 ]
[ 23979-41-1 ]

Reference： [1]Tetrahedron Letters,1986,vol. 27,p. 1763 - 1766

9
[ 83022-46-2 ]
[ 30012-51-2 ]

Yield	Reaction Conditions	Operation in experiment
84%	With diethylamino-sulfur trifluoride In dichloromethane at 25℃; for 2.5h;

Reference： [1]Yamauchi, Takayoshi; Hattori, Kaneaki; Ikeda, Shun-ichi; Tamaki, Kentaro [Journal of the Chemical Society. Perkin transactions I, 1990, # 6, p. 1683 - 1685]

10
[ 80336-55-6 ]
[ 30012-51-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With silver tetrafluoroborate; trimethyl orthoformate In methanol at 40℃; for 1h;
	In toluene at 115℃; for 0.5h;

Reference： [1]Giordano, Claudio; Castaldi, Graziano; Casagrande, Francesco; Belli, Aldo [Journal of the Chemical Society. Perkin transactions I, 1982, # 11, p. 2575 - 2582]
[2]Castaldi, Graziano; Belli, Aldo; Uggeri, Fulvio; Giordano, Claudio [Journal of Organic Chemistry, 1983, vol. 48, # 24, p. 4658 - 4661]

11
[ 81112-05-2 ]
[ 30012-51-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	With calcium carbonate In water; N,N-dimethyl-formamide for 5h; Heating;

Reference： [1]Tsuchihashi, Gen-ichi; Kitajima, Koji; Mitamura, Shuichi [Tetrahedron Letters, 1981, vol. 22, # 43, p. 4305 - 4308]

12
[ 23981-48-8 ]
[ 616-38-6 ]
[ 57625-74-8 ]
[ 30012-51-2 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1994,p. 1323 - 1328

13
[ 76145-94-3 ]
[ 2700-47-2 ]
[ 30012-51-2 ]
[ 76145-97-6 ]

Reference： [1]Tetrahedron,1994,vol. 50,p. 1243 - 1260

14
[ 2700-47-2 ]
[ 149-73-5 ]
[ 30012-51-2 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1990,vol. 29,p. 304 - 309

15
[ 23981-48-8 ]
[ 616-38-6 ]
[ 30012-51-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate at 220℃; for 6h;
	With potassium carbonate at 220℃; for 7.5h; Autoclave; Inert atmosphere; Green chemistry;

Reference： [1]Bomben, Andrea; Selva, Maurizio; Tundo, Pietro [Recueil des Travaux Chimiques des Pays-Bas, 1996, vol. 115, # 4, p. 256 - 260]
[2]Tundo, Pietro; Selva, Maurizio; Bomben, Andrea; Belica, Peter; Koehler, Robert; Wolff, Steven [Organic Syntheses, 1999, vol. 76, p. 169 - 169]

16
[ 67-56-1 ]
[ 201230-82-2 ]
1-(6-methoxy-2-naphthyl)ethanol [ No CAS ]
[ 30012-51-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With p-Ts (cat.); triphenylphosphine In 1,4-dioxane at 100℃; for 24h;
93 % Chromat.	With 1,4:3,6-dianhydro-2,5-dideoxy-2,5-bis-(diphenylphosphino)-L-iditol; trifluoroacetic acid; copper dichloride; palladium dichloride In butanone at 100℃;

Reference： [1]Zhou, Hongying; Cheng, Jing; Lu, Shijie; Fu, Hongxiang; Wang, Hanqing [Journal of Organometallic Chemistry, 1998, vol. 556, # 1-2, p. 239 - 242]
[2]Xie, Bao-Han; Xia, Chun-Gu; Lu, Shi-Jie; Chen, Ke-Jun; Kou, Yuan; Yuan-Qi, Yin [Tetrahedron Letters, 1998, vol. 39, # 40, p. 7365 - 7368]

17
[ 67-56-1 ]
[ 201230-82-2 ]
[ 108781-65-3 ]
[ 30012-51-2 ]
[ 63444-51-9 ]
[ 132367-16-9 ]

Reference： [1]Journal of Organometallic Chemistry,1998,vol. 556,p. 239 - 242

18
[ 30012-51-2 ]
[ 37414-52-1 ]

Yield	Reaction Conditions	Operation in experiment
92.3%	With lithium aluminium tetrahydride In diethyl ether
80%	With lithium aluminium tetrahydride Inert atmosphere;
	With sodium tetrahydroborate In methanol for 4h;

Reference： [1]Koul, Surrinder; Koul, Jawahir Lal; Singh, Budh; Kapoor, Munish; Parshad, Rajinder; Manhas, Kuldeep S.; Taneja, Subhash C.; Qazi, Ghulam N. [Tetrahedron Asymmetry, 2005, vol. 16, # 15, p. 2575 - 2591]
[2]Burns, Alexander S.; Wagner, Alexander J.; Fulton, Jennifer L.; Young, Kyle; Zakarian, Armen; Rychnovsky, Scott. D. [Organic Letters, 2017, vol. 19, # 11, p. 2953 - 2956]
[3]Basak, Amit; Nag, Ahindra; Bhattacharya, Gautam; Mandal, Subrata; Nag, Sikha [Tetrahedron Asymmetry, 2000, vol. 11, # 11, p. 2403 - 2407]

19
[ 30012-51-2 ]
[ 26159-35-3 ]

Yield	Reaction Conditions	Operation in experiment
	With Sulfobalus solfataricus P₁ (Sso EST₁) In phosphate buffer for 16h;
	With methanol; sodium at 23℃; Glass beads; Ultrasonic bath;	4 Example 4; Deracemization of methyl (/?S)-2-(6-methoxynaphthalen-2-yl)propanoate; In a standard 10 mL sample vial were added glass beads (0 2-2.5 mm, Aldrich, 8.7 g), methyl (RS)-2-(6-methoxynaphthalen-2-yl)propanoate (0.7553 g), methyl (S)-2-(6- methoxynaphthalen-2-yl)propanoate (0.0030 g) and NaOMe/MeOH (6.302 g from a stock solution prepared by dissolving 2.2 g Na in 45 mL MeOH). The sample vial was closed with a septum, and placed on an Elma Transsonic T470/H ultrasonic bath. The bath was kept at a constant temperature of 23°C using a cooling spiral that was attached to a Julabo F25 thermostat bath. For sampling, 0.3 mL of the slurry was taken using a syringe, filtered on a P4 glass filter and washed with MeOH (approx. 2 mL). The chiral purity was measured using chiral HPLC. 1H NMR (400 MHz, CDCI3): δ = 7.62 (s, 1 H), 7.57 (d, 1 H, J = 8.5 Hz), 7.48-7.45 (m, 2H), 7.18 (d, 1 H, J = 2.6 Hz), 6.89 (d, 1 H, J = 2.4 Hz), 3.71 (q, 1 H, J = 7.1 Hz), 3.36 (s, 3H), 3.28 (s, 3H), 1.52 (d, 3H, J = 7.1 Hz). HPLC analysis was performed on Chiralcel-OJ (250x4.6 mm ID) column, eluent n-hexane/2- propanol 98/2 v/v%, flow 1 mL.min'1 , room temperature, detection at λ=254 nm. Retention times methyl (S)-2-(6-methoxynaphthalen-2-yl)propanoate 10.5 min, methyl (fi)-2-(6-methoxynaphthalen-2-yl)piOpanoate 1 1.4 min. The results of this experiment are given in Figure 1. It can be seen from this Figure that already an initial enantiomeric excess of 1.5% results in the exponential evolution to an enantiopure methyl (S)-2-(6- methoxynaphthalen-2-yl)propanoate solid phase.

Reference： [1]Sehgal, Amitabh C.; Kelly, Robert M. [Journal of the American Chemical Society, 2002, vol. 124, # 28, p. 8190 - 8191]
[2]Current Patent Assignee: KONINKLIJKE DSM N.V. - WO2010/89343, 2010, A1 Location in patent: Page/Page column 9-10

20
[ 30012-51-2 ]
[ 863224-86-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	With perchloryl fluoride; lithium diisopropyl amide In tetrahydrofuran; hexane at -40℃; for 1h;

Reference： [1]Fujisawa, Hidehito; Fujiwara, Tomoya; Takeuchi, Yoshio; Omata, Kenji [Chemical and Pharmaceutical Bulletin, 2005, vol. 53, # 5, p. 524 - 528]

21
[ 30012-51-2 ]
[ 74-88-4 ]
[ 69337-84-4 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: methyl 2-(6-methoxy-2-naphthyl)propionate With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium diisopropyl amide In tetrahydrofuran at -78℃; Stage #2: methyl iodide In tetrahydrofuran
	With N,N,N,N,N,N-hexamethylphosphoric triamide; acetic acid; lithium diisopropyl amide In tetrahydrofuran; hexane; cyclohexane	22 α,α-Dimethyl-6-(2-quinolinylmethoxy)-2-naphthaleneacetic acid EXAMPLE 22 α,α-Dimethyl-6-(2-quinolinylmethoxy)-2-naphthaleneacetic acid To a solution of α-methyl-6-methoxy-2-naphthaleneacetic acid methyl ester (12.2 g, 50 mmol) in tetrahydrofuran (100 ml) at -70 ° c. is added a solution of lithium diisopropylamide in cyclohexane (50 ml, 1.5 equiv). After 20 min, methyl iodide (4.0 ml, 1.3 equiv) is added followed by hexamethylphosphoramide (20 ml). After allowing the reaction mixture to warm to room temperature and stir 16 hours, the reaction is quenched by addition of acetic acid (4.3 ml, 75 mmol). The solvent is then removed and the residue is partitioned between ethyl acetate and water. The organic layer is washed with water 3 times and finally with brine. After drying over magnesium sulfate, the organic extract is evaporated to afford a crude solid. Recrystallization of this solid from hexane affords 8.56 g (66%) of α,α-dimethyl-6-methoxy-2-naphthaleneacetic acid methyl ester as white crystals, m.p. 97°-98° C.
	With acetic acid; lithium diisopropyl amide In tetrahydrofuran; hexane; cyclohexane	22 α,α-Dimethyl-6-(2-quinolinylmethoxy)-2-naphthaleneacetic acid EXAMPLE 22 α,α-Dimethyl-6-(2-quinolinylmethoxy)-2-naphthaleneacetic acid To a solution of (α-methyl-6-methoxy-2-naphthaleneacetic acid methyl ester (12.2 g, 50 mmol) in tetrahydrofuran (100 ml) at -70° C. is added a solution of lithium diisopropylamide in cyclohexane (50 ml, 1.5 equiv). After 20 minutes, methyl iodide (4.0 ml, 1.3 equiv) is added followed by hexamethylphosphoraniide (20 ml). After allowing the reaction mixture to warm to room temperature and stir 16 hours, the reaction is quenched by addition of acetic acid (4.3 ml, 75 mmol). The solvent is then removed and the residue is partitioned between ethyl acetate and water. The organic layer is washed with water 3 times and finally with brine. After drying over magnesium sulfate, the organic extract is evaporated to afford a crude solid. Recrystallization of this solid from hexane affords 8.56 g (66%) of α,α-dimethyl-6-methoxy-2-naphthaleneacetic acid methyl ester as white crystals, m.p. 97°-98° C.

	With N,N,N,N,N,N-hexamethylphosphoric triamide; acetic acid; lithium diisopropyl amide In tetrahydrofuran; hexane; cyclohexane	22 α, α-Dimethyl-6-(2-quinolinylmethoxy)-2-naphthaleneacetic acid EXAMPLE 22 α, α-Dimethyl-6-(2-quinolinylmethoxy)-2-naphthaleneacetic acid To a solution of α-methyl-6-methoxy-2-naphthaleneacetic acid methyl ester (12.2 g, 50 mmol) in tetrahydrofuran (100 ml) at -70° C. is added a solution of lithium diisopropylamide in cyclohexane (50 ml, 1.5 equiv). After 20 min, methyl iodide (4.0 ml, 1.3 equiv) is added followed by hexamethylphosphoramide (20 ml). After allowing the reaction mixture to warm to room temperature and stir 16 hours, the reaction is quenched by addition of acetic acid (4.3 ml, 75 mmol). The solvent is then removed and the residue is partitioned between ethyl acetate and water. The organic layer is washed with water 3 times and finally with brine. After drying over magnesium sulfate, the organic extract is evaporated to afford a crude solid. Recrystallization of this solid from hexane affords 8.56 g (66%) of α,α-dimethyl-6-methoxy-2-naphthaleneacetic acid methyl ester as white crystals, m.p. 97°-98° C.
	Stage #1: methyl 2-(6-methoxy-2-naphthyl)propionate With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran at -78 - 0℃; for 0.5h; Inert atmosphere; Stage #3: methyl iodide In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere;

Reference： [1]Stock, Nicholas; Munoz, Benito; Wrigley, Jonathan D.J.; Shearman, Mark S.; Beher, Dirk; Peachey, James; Williamson, Toni L.; Bain, Gretchen; Chen, Weichao; Jiang, Xiaohui; St-Jacques, Rene; Prasit, Peppi [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 8, p. 2219 - 2223]
[2]Current Patent Assignee: PFIZER INC - US5208344, 1993, A
[3]Current Patent Assignee: PFIZER INC - US5250693, 1993, A
[4]Current Patent Assignee: PFIZER INC - US5084575, 1992, A
[5]Windsor, Matthew A.; Hermanson, Daniel J.; Kingsley, Philip J.; Xu, Shu; Crews, Brenda C.; Ho, Winnie; Keenan, Catherine M.; Banerjee, Surajit; Sharkey, Keith A.; Marnett, Lawrence J. [ACS Medicinal Chemistry Letters, 2012, vol. 3, # 9, p. 759 - 763]

22
[ 23981-48-8 ]
[ 74-88-4 ]
[ 30012-51-2 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: methyl 6-methoxy-2-naphthylacetate With potassium hexamethylsilazane In 1,2-dimethoxyethane; toluene at -78℃; Stage #2: methyl iodide In 1,2-dimethoxyethane; toluene at -78℃; Further stages.;

Reference： [1]Sarakinos, Georgios; Corey [Organic Letters, 1999, vol. 1, # 11, p. 1741 - 1744]

23
[ 30012-51-2 ]
[ 22204-53-1 ]
[ 23979-41-1 ]
[ 81623-44-1 ]
[ 26159-35-3 ]

Reference： [1]Journal of Catalysis,2007,vol. 247,p. 194 - 200

24
[ 30012-51-2 ]
2-fluoro-2-(6-methoxy-naphthalen-2-yl)-propionyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 96 percent / lithium diisopropylamide; FClO₃ / tetrahydrofuran; hexane / 1 h / -40 °C 2: 95 percent / aq. KOH / methanol / 20 °C 3: (COCl)2; N,N-dimethylformamide / tetrahydrofuran / 0 - 20 °C

Reference： [1]Fujisawa, Hidehito; Fujiwara, Tomoya; Takeuchi, Yoshio; Omata, Kenji [Chemical and Pharmaceutical Bulletin, 2005, vol. 53, # 5, p. 524 - 528]

25
[ 30012-51-2 ]
(S)-(+)-2-fluoro-2-[6-methoxy(2-naphthyl)]propionic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 96 percent / lithium diisopropylamide; FClO₃ / tetrahydrofuran; hexane / 1 h / -40 °C 2: 95 percent / aq. KOH / methanol / 20 °C 3: (COCl)2; N,N-dimethylformamide / tetrahydrofuran / 0 - 20 °C 4: N,N-dimethylaminopyridine; Et₃N / tetrahydrofuran / 20 °C 5: 80 percent / aq. KOH / methanol / 20 °C

Reference： [1]Fujisawa, Hidehito; Fujiwara, Tomoya; Takeuchi, Yoshio; Omata, Kenji [Chemical and Pharmaceutical Bulletin, 2005, vol. 53, # 5, p. 524 - 528]

26
[ 30012-51-2 ]
(R)-(-)-2-fluoro-2-[6-methoxy(2-naphthyl)]propionic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 96 percent / lithium diisopropylamide; FClO₃ / tetrahydrofuran; hexane / 1 h / -40 °C 2: 95 percent / aq. KOH / methanol / 20 °C 3: (COCl)2; N,N-dimethylformamide / tetrahydrofuran / 0 - 20 °C 4: N,N-dimethylaminopyridine; Et₃N / tetrahydrofuran / 20 °C 5: 78 percent / aq. KOH / methanol / 20 °C

Reference： [1]Fujisawa, Hidehito; Fujiwara, Tomoya; Takeuchi, Yoshio; Omata, Kenji [Chemical and Pharmaceutical Bulletin, 2005, vol. 53, # 5, p. 524 - 528]

27
[ 30012-51-2 ]
[ 863224-95-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 96 percent / lithium diisopropylamide; FClO₃ / tetrahydrofuran; hexane / 1 h / -40 °C 2: 95 percent / aq. KOH / methanol / 20 °C 3: (COCl)2; N,N-dimethylformamide / tetrahydrofuran / 0 - 20 °C 4: N,N-dimethylaminopyridine; Et₃N / tetrahydrofuran / 20 °C

Reference： [1]Fujisawa, Hidehito; Fujiwara, Tomoya; Takeuchi, Yoshio; Omata, Kenji [Chemical and Pharmaceutical Bulletin, 2005, vol. 53, # 5, p. 524 - 528]

28
[ 30012-51-2 ]
[ 863224-96-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 96 percent / lithium diisopropylamide; FClO₃ / tetrahydrofuran; hexane / 1 h / -40 °C 2: 95 percent / aq. KOH / methanol / 20 °C 3: (COCl)2; N,N-dimethylformamide / tetrahydrofuran / 0 - 20 °C 4: N,N-dimethylaminopyridine; Et₃N / tetrahydrofuran / 20 °C

Reference： [1]Fujisawa, Hidehito; Fujiwara, Tomoya; Takeuchi, Yoshio; Omata, Kenji [Chemical and Pharmaceutical Bulletin, 2005, vol. 53, # 5, p. 524 - 528]

29
[ 30012-51-2 ]
[ 180293-50-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 96 percent / lithium diisopropylamide; FClO₃ / tetrahydrofuran; hexane / 1 h / -40 °C 2: 95 percent / aq. KOH / methanol / 20 °C

Reference： [1]Fujisawa, Hidehito; Fujiwara, Tomoya; Takeuchi, Yoshio; Omata, Kenji [Chemical and Pharmaceutical Bulletin, 2005, vol. 53, # 5, p. 524 - 528]

30
[ 30012-51-2 ]
[ 76842-29-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 92.3 percent / LiAlH₄ / diethyl ether 2: 97.2 percent / DMAP / 0.5 h / 50 °C
	Multi-step reaction with 2 steps 1: sodium borohydride / methanol / 4 h 2: triethylamine; DMAP / CH₂Cl₂ / 1 h / 20 °C

Reference： [1]Koul, Surrinder; Koul, Jawahir Lal; Singh, Budh; Kapoor, Munish; Parshad, Rajinder; Manhas, Kuldeep S.; Taneja, Subhash C.; Qazi, Ghulam N. [Tetrahedron Asymmetry, 2005, vol. 16, # 15, p. 2575 - 2591]
[2]Basak, Amit; Nag, Ahindra; Bhattacharya, Gautam; Mandal, Subrata; Nag, Sikha [Tetrahedron Asymmetry, 2000, vol. 11, # 11, p. 2403 - 2407]

31
[ 3900-45-6 ]
[ 30012-51-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 100 percent / H₂ / 5 percent Pd/C / tetrahydrofuran 2: 93 percent Chromat_. / PdCl₂, CuCl₂, TFA, 1,4:3,6-dianhydro-2,5-dideoxy-2,5-bis(diphenylphosphino)-L-iditol / butan-2-one / 100 °C / 600048 Torr

Reference： [1]Xie, Bao-Han; Xia, Chun-Gu; Lu, Shi-Jie; Chen, Ke-Jun; Kou, Yuan; Yuan-Qi, Yin [Tetrahedron Letters, 1998, vol. 39, # 40, p. 7365 - 7368]

32
[ 5111-65-9 ]
[ 30012-51-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 63 percent / Mg / tetrahydrofuran / 4 h / -40 °C 2: propylene oxide / methanol / Irradiation; pH neutral
	Multi-step reaction with 2 steps 1.1: palladium diacetate; triethylamine; C₂₂H₂₇P / 1,4-dioxane; Hexadecane / 20 h / 120 °C / 15001.5 Torr / Schlenk technique; Inert atmosphere 2.1: hydrogenchloride / water / 20 h / 30003 Torr / Schlenk technique; Inert atmosphere 2.2: 2 h / Schlenk technique; Inert atmosphere; Reflux

Reference： [1]Sonawane, Harikisan; Bellur, Nanjundiah S.; Kulkarni, Dilip G.; Ayyangar, Nagaraj R. [Tetrahedron, 1994, vol. 50, # 4, p. 1243 - 1260]
[2]Neumann, Helfried; Sergeev, Alexey G.; Spannenberg, Anke; Beller, Matthias [Molecules, 2020, vol. 25, # 15]

33
1-(6-methoxynaphthalen-2-yl)ethan-1-ol [ No CAS ]
[ 30012-51-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 100 percent / pyridine 2: 43 percent / Sn(OTf)4 / CH₂Cl₂ / 3.5 h / -78 °C 3: 90 percent / aq. potassium hydroxide / 5 h / Heating 4: 65 percent / diethyl ether / 1 h / 0 °C
	Multi-step reaction with 4 steps 1: 100 percent / pyridine 2: 57 percent / SnCl₄ / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 1 h; room temp., 1 h 3: 90 percent / aq. potassium hydroxide / 5 h / Heating 4: 65 percent / diethyl ether / 1 h / 0 °C
	Multi-step reaction with 4 steps 1: 100 percent / pyridine 2: 89 percent / tetrahydrofuran; benzene / 36 h / Ambient temperature 3: 90 percent / aq. potassium hydroxide / 5 h / Heating 4: 65 percent / diethyl ether / 1 h / 0 °C

	Multi-step reaction with 4 steps 1: 100 percent / pyridine 2: 39 percent / SnCl₄-pyridine / CH₂Cl₂ / -78 deg C, 0.5 h; 0 deg C, 1.3 h 3: 90 percent / aq. potassium hydroxide / 5 h / Heating 4: 65 percent / diethyl ether / 1 h / 0 °C
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / Schlenk technique; Inert atmosphere 1.2: 6 h / 20 °C / Cooling 2.1: palladium diacetate; toluene-4-sulfonic acid; bis[2-(diphenylphosphino)phenyl] ether / toluene / 18 h / 130 °C / 18751.9 Torr / Autoclave
	Multi-step reaction with 2 steps 1.1: Quinuclidine; sodium tetraphenyl borate; [4,4'-bis(1,1-dimethylethyl)-2,2'-bipyridine-N₁,N₁']bis[2-(2-pyridinyl-N)phenyl-C]iridium(III) hexafluorophosphate / N,N-dimethyl-formamide / 40 h / 760.05 Torr / Schlenk technique; Sealed tube; Irradiation; Glovebox 1.2: 0.25 h 2.1: diazomethyl-trimethyl-silane / toluene / 1 h / 20 °C

Reference： [1]Hiyama; Inoue [Synthesis, 1986, vol. NO. 8, # 8, p. 689 - 691]
[2]Hiyama; Inoue [Synthesis, 1986, vol. NO. 8, # 8, p. 689 - 691]
[3]Hiyama; Inoue [Synthesis, 1986, vol. NO. 8, # 8, p. 689 - 691]
[4]Hiyama; Inoue [Synthesis, 1986, vol. NO. 8, # 8, p. 689 - 691]
[5]Beller, Matthias; Jackstell, Ralf; Maes, Bert U. W.; Schneider, Carolin [European Journal of Organic Chemistry, 2020]
[6]Jiang, Yi-Qian; Lan, Yu; Li, Shi-Jun; Li, Wen-Duo; Li, Yan-Lin; Wu, Yang; Xia, Ji-Bao [Journal of the American Chemical Society, 2021]

34
1-(6-methoxynaphthalen-2-yl)ethyl acetate [ No CAS ]
[ 30012-51-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 43 percent / Sn(OTf)4 / CH₂Cl₂ / 3.5 h / -78 °C 2: 90 percent / aq. potassium hydroxide / 5 h / Heating 3: 65 percent / diethyl ether / 1 h / 0 °C
	Multi-step reaction with 3 steps 1: 57 percent / SnCl₄ / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 1 h; room temp., 1 h 2: 90 percent / aq. potassium hydroxide / 5 h / Heating 3: 65 percent / diethyl ether / 1 h / 0 °C
	Multi-step reaction with 3 steps 1: 89 percent / tetrahydrofuran; benzene / 36 h / Ambient temperature 2: 90 percent / aq. potassium hydroxide / 5 h / Heating 3: 65 percent / diethyl ether / 1 h / 0 °C

Multi-step reaction with 3 steps 1: 39 percent / SnCl₄-pyridine / CH₂Cl₂ / -78 deg C, 0.5 h; 0 deg C, 1.3 h 2: 90 percent / aq. potassium hydroxide / 5 h / Heating 3: 65 percent / diethyl ether / 1 h / 0 °C

Reference： [1]Hiyama; Inoue [Synthesis, 1986, vol. NO. 8, # 8, p. 689 - 691]
[2]Hiyama; Inoue [Synthesis, 1986, vol. NO. 8, # 8, p. 689 - 691]
[3]Hiyama; Inoue [Synthesis, 1986, vol. NO. 8, # 8, p. 689 - 691]
[4]Hiyama; Inoue [Synthesis, 1986, vol. NO. 8, # 8, p. 689 - 691]

35
[ 86603-94-3 ]
[ 30012-51-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 90 percent / aq. potassium hydroxide / 5 h / Heating 2: 65 percent / diethyl ether / 1 h / 0 °C

Reference： [1]Hiyama; Inoue [Synthesis, 1986, vol. NO. 8, # 8, p. 689 - 691]

36
[ 27602-75-1 ]
[ 30012-51-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NaHSO₃ / methanol; H₂O 2: methanol

Reference： [1]Wuts, Peter G. M.; Bergh, Carol L. [Tetrahedron Letters, 1986, vol. 27, # 34, p. 3995 - 3998]

37
(CHCl₃) [ No CAS ]
[ 30012-51-2 ]
[ 23981-80-8 ]

Yield	Reaction Conditions	Operation in experiment
63%	With hydrogenchloride In 1,2-dimethoxyethane; water	9 EXAMPLE 9 STR23 EXAMPLE 9 STR23 A mixture of 90 mg (0.37 mmol) of methyl (+)-α-(6-methoxy-2-naphthyl)propionate having a 100% optical purity [α]D20 +78.2° (CHCl3)], 1 ml of 12N aqueous hydrochloric acid and 1 ml of dimethoxyethane was stirred at 50° C. for 23 hours. After adding 10 ml of water, the mixture was extracted with diethyl ether (8 ml*3), and the extract was washed with water (3 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography [silica gel, hexane+ethyl acetate (1:2)] to obtain 49 mg of (+)-α-(6-methoxy-2-naphthyl)propionic acid as colorless crystals. Yield, 63%. Melting Point: 155°-157° C. [α]D20 +67.2° (c=1.10, CHCl3).

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US4496755, 1985, A

38
[ 67333-31-7 ]
[ 30012-51-2 ]

Yield	Reaction Conditions	Operation in experiment
68%	In methanol; dichloromethane	32 EXAMPLE 32 EXAMPLE 32 Methyl α-methylthio-α-(6-methoxy-2-naphthyl) propionate (372 mg) was dissolved in 2 ml of methanol, and 10 ml of a methanol suspension of 5.0 cc of Raney nickel (W-II) was added, and the mixture was stirred at room temperature for 15 hours. The insoluble matter was separated by filtration, and the filtrate was concentrated under reduced pressure. Methylene chloride was added to the residue. The insoluble matter was separated by filtration. The filtrate was concentrated under reduced pressure, and the residue was chromatographed on a silica gel column using benzene as an eluent to afford 212 mg of methyl α-(6-methoxy-2-naphthyl)propionate as colorless crystals in a yield of 68%. The product had a melting point (from petroleum ether) of 67° to 69° C.

Reference： [1]Current Patent Assignee: SAGAMI CHEMICAL RESEARCH INSTITUTE - US4242519, 1980, A

39
[ 22204-53-1 ]
[ 30012-51-2 ]

Yield	Reaction Conditions	Operation in experiment
93.3%	With hydrogenchloride; sodium hydrogencarbonate In dichloromethane; water; 1,3,5-trimethyl-benzene	15 d-2-(6-Methoxy-2-naphthyl)propionic acid, methyl ester EXAMPLE 15 d-2-(6-Methoxy-2-naphthyl)propionic acid, methyl ester 20.8 Ml of mesitylene are added to a solution of 32.3 g of the methyl ester of the d-2-(6-methoxy-2-naphthyl)propionic acid dissolved in 130 ml of methylene chloride. 20 Grams of anhydrous aluminum chloride are added portionwise under stirring to the reaction mixture cooled to -5° C., while keeping the temperature at about 10° C. The reaction mixture is kept under stirring for one hour at about 10° C. and then is poured into a mixture made of 100 g of crushed ice and of 15 ml of a 35% (w/v) aqueous solution of hydrochloric acid. The layers are separated after 15 minutes of stirring, the aqueous phase is discarded while the organic layer is twice washed with 100 ml of a 1N aqueous solution of hydrochloric acid, once with 100 ml of water and once with 100 ml of a 8% (w/v) aqueous solution of sodium bicarbonate. The organic solution is dried over anhydrous sodium sulfate and concentrated to dryness under vacuum. The residue is crystallized by n-hexane obtaining 22.8 g of pure product having [α]D20 =+80.3° (C=1% in chloroform) with a yield equal to 93.3%.

Reference： [1]Current Patent Assignee: ALFA CHEMICALS ITALIANA S.P.A. - US5107013, 1992, A

40
[ 27655-95-4 ]
[ 30012-51-2 ]

Yield	Reaction Conditions	Operation in experiment
86.7%	With hydrogenchloride; sodium hydrogencarbonate In dichloromethane; water; 1,3,5-trimethyl-benzene	13 2-(6-Methoxy-2-naphthyl)propionic acid, methyl ester EXAMPLE 13 2-(6-Methoxy-2-naphthyl)propionic acid, methyl ester 10.4 Ml of mesitylene are added to a solution containing 16.1 g of the methyl ester of the 2-(5-bromo-6-methoxy-2-naphthyl)propionic acid dissolved in 65 ml of methylene chloride. 13.5 Grams of anhydrous aluminum chloride are added portionwise under stirring to the reaction mixture cooled to -5°C, while keeping the temperature at about 15°C. The reaction mixture is kept under stirring at about 15°C for 2 hours and then is poured into a mixture made of 68 g of crushed ice and 15 ml of a 35% (w/v) aqueous solution of hydrochloric acid. The layers are separated, the aqueous layer is extracted with 30 ml of methylene chloride and then is discarded. The organic layers are collected, first washed with 50 ml of a 1 N aqueous solution of hydrochloric acid, then with 50 ml of water and lastly with 50 ml of a 8% (w/v) aqueous solution of sodium bicarbonate. The organic solution is then dried over anhydrous sodium sulfate and concentrated to dryness under vacuum. The residue is crystallized from n-hexane obtaining 10.6 g of product with a yield equal to 86.7%.
86.7%	With hydrogenchloride; sodium hydrogencarbonate In dichloromethane; water; 1,3,5-trimethyl-benzene	13 2-(6-Methoxy-2-naphthyl)propionic acid, methyl ester EXAMPLE 13 2-(6-Methoxy-2-naphthyl)propionic acid, methyl ester 10.4 Ml of mesitylene are added to a solution containing 16.1 g of the methyl ester of the 2-(5-bromo-6-methoxy-2-naphthyl)propionic acid dissolved in 65 ml of methylene chloride. 13.5 Grams of anhydrous aluminum chloride are added portionwise under stirring to the reaction mixture cooled to -5° C., while keeping the temperature at about 15° C. The reaction mixture is kept under stirring at about 15° C. for 2 hours and then is poured into a mixture made of 68 g of crushed ice and 15 ml of a 35% (w/v) aqueous solution of hydrochloric acid. The layers are separated, the aqueous layer is extracted with 30 ml of methylene chloride and then is discarded. The organic layers are collected, first washed with 50 ml of a 1N aqueous solution of hydrochloric acid, then with 50 ml of water and lastly with 50 ml of a 8% (w/v) aqueous solution of sodium bicarbonate. The organic solution is then dried over anhydrous sodium sulfate and concentrated to dryness under vacuum. The residue is crystallized from n-hexane obtaining 10.6 g of product with a yield equal to 86.7%.
32.7%	With hydrogenchloride; sodium hydrogencarbonate In dichloromethane; water; 1,3,5-trimethyl-benzene	14 2-(6-Methoxy-2-naphthyl)propionic acid, methyl ester EXAMPLE 14 2-(6-Methoxy-2-naphthyl)propionic acid, methyl ester 16.1 Grams of the methyl ester of the 2-(5-bromo-6-methoxy-2-naphthyl)propionic acid are dissolved in 65 ml of methylene chloride and then 10.4 ml of mesitylene and 12 ml of anhydrous titanium tetrachloride are added while keeping the temperature at about 20° C. The reaction mixture is kept under stirring at room temperature for 80 hours and then is poured into a mixture made of 68 g of crushed ice and of 15 ml of a 35% (w/v) aqueous solution of hydrochloric acid. The layers are separated after 15 minutes of stirring, the aqueous layer is extracted with 30 ml of methylene chloride and then is discarded. The organic layers are collected, first washed with 50 ml of a 1N aqueous solution of hydrochloric acid, then with 50 ml of water and lastly with 50 ml of a 8% (w/v) aqueous solution of sodium bicarbonate. The organic solution is dried over anhydrous sodium sulfate and then is evaporated under vacuum. The residue is crystallized first with n-hexane and then with methyl alcohol obtaining 4 g of product with a yield equal to 32.7%.

32.7%

With hydrogenchloride; sodium hydrogencarbonate In dichloromethane; water; 1,3,5-trimethyl-benzene

14 2-(6-Methoxy-2-naphthyl)propionic acid, methyl ester EXAMPLE 14 2-(6-Methoxy-2-naphthyl)propionic acid, methyl ester 16.1 Grams of the methyl ester of the 2-(5-bromo-6-methoxy-2-naphthyl)propionic acid are dissolved in 65 ml of methylene chloride and then 10.4 ml of mesitylene and 12 ml of anhydrous titanium tetrachloride are added while keeping the temperature at about 20°C. The reaction mixture is kept under stirring at room temperature for 80 hours and then is poured into a mixture made of 68 g of crushed ice and of 15 ml of a 35% (w/v) aqueous solution of hydrochloric acid. The layers are separated after 15 minutes of stirring, the aqueous layer is extracted with 30 ml of methylene chloride and then is discarded. The organic layers are collected, first washed with 50 ml of a 1 N aqueous solution of hydrochloric acid, then with 50 ml of water and lastly with 50 ml of a 8% (w/v) aqueous solution of sodium bicarbonate. The organic solution is dried over anhydrous sodium sulfate and then is evaporated under vacuum. The residue is crystallized first with n-hexane and then with methyl alcohol obtaining 4 g of product with a yield equal to 32.7%.

Reference： [1]Current Patent Assignee: ALFA CHEMICALS ITALIANA S.P.A. - EP440930, 1991, A2
[2]Current Patent Assignee: ALFA CHEMICALS ITALIANA S.P.A. - US5107013, 1992, A
[3]Current Patent Assignee: ALFA CHEMICALS ITALIANA S.P.A. - US5107013, 1992, A
[4]Current Patent Assignee: ALFA CHEMICALS ITALIANA S.P.A. - EP440930, 1991, A2

41
[ 23981-80-8 ]
[ 30012-51-2 ]

Yield	Reaction Conditions	Operation in experiment
93.3%	With hydrogenchloride; sodium hydrogencarbonate;aluminium trichloride; In dichloromethane; water; 1,3,5-trimethyl-benzene;	EXAMPLE 15 d-2-(6-Methoxy-2-naphthyl)propionic acid, methyl ester 20.8 Ml of mesitylene are added to a solution of 32.3 g of the methyl ester of the d-2-(6-methoxy-2-naphthyl) propionic acid dissolved in 130 ml of methylene chloride. 20 Grams of anhydrous aluminum chloride are added portionwise under stirring to the reaction mixture cooled to -5C, while keeping the temperature at about 10C. The reaction mixture is kept under stirring for one hour at about 10C and then is poured into a mixture made of 100 g of crushed ice and of 15 ml of a 35% (w/v) aqueous solution of hydrochloric acid. The layers are separated after 15 minutes of stirring, the aqueous phase is discarded while the organic layer is twice washed with 100 ml of a 1 N aqueous solution of hydrochloric acid, once with 100 ml of water and once with 100 ml of a 8% (w/v) aqueous solution of sodium bicarbonate. The organic solution is dried over anhydrous sodium sulfate and concentrated to dryness under vacuum. The residue is crystallized by n-hexane obtaining 22.8 g of pure product having (C = 1% in chloroform) with a yield equal to 93.3%.

Reference： [1]Patent: EP440930,1991,A2

42
[ 30012-51-2 ]
[ 57475-91-9 ]

Yield	Reaction Conditions	Operation in experiment
76%	With hydrazine hydrate In methanol for 24h; Reflux;	3.2 3.2. Synthesis of the intermediary 2--(6-methoxy-2-naphtyl) propanohydrazide In a 250 mL flask connected to a reflux condenser there were added 0.5 g of naproxen ester, 50 mL of methanol and 8 mL of hydrazine hydrate 25%. The reaction is kept under reflux and stirring for 24 hours until thin layer chromatography indicates the completion of the reaction (Mobile phase: 1:1, hexane:ethyl acetate). The product was obtained by reduction of the solvent at reduced pressure, followed by addition of about 4 mL of water/ice. There is formation of a precipitate that is filtered and washed with ice water to provide 0.38 g of a white solid with melting range between 129° - 133° C. (C14H16N2O2 ; MW= 244,11; yield: 76%). The NMR H1 spectrum (400MHz, DMSOd) was as follows: δ 1.41 (d; 3H); 3.65 (q; 1H); 3.86 (s; 3H); 4.22 (s; 1H); 7.13 (dd; 1H; Jorto=9 Hz and Jmeta=2.56 Hz); 7.26 (d; 1H; Jmeta=2.39 Hz); 7.45 (dd; 1H; Jorto=8.53 Hz and Jmeta=1.88 Hz); 7.71 (d; 1H); 7.73 (d; 1H; Jorto= 8.53 Hz); 7.77 (d; 1H; Jorto= 9 Hz) ppm. The IR spectrum (KBr pellet) was as follows: ν 3296 (N-H), 2956 (C-H, CH2 and CH3), ν 1637 (C=O hydrazide), δ 1604, 1450 (C-H aromatic), ν 1261 (C-O), ν 1213 (-CN) cm-1.
76%	With hydrazine hydrate In methanol for 24h; Reflux;	3.2 In a 250 mL flask connected to a reflux condenser there were added 0.5 g of naproxen ester, 50 mL of methanol and 8 mL of hydrazine hydrate 25%. The reaction is kept under reflux and stirring for 24 hours until thin layer chromatography indicates the completion of the reaction (Mobile phase: 1:1, hexane:ethyl acetate).The product was obtained by reduction of the solvent at reduced pressure, followed by addition of about 4 mL of water/ice. There is formation of a precipitate that is filtered and washed with ice water to provide 0.38 g of a white solid with melting range between 129°-133° C. (C14H16N2O2; MW=244,11; yield: 76%).The NMR H1 spectrum (400 MHz, DMSOd) was as follows: δ 1.41 (d; 3H); 3.65 (q; 1H); 3.86 (s; 3H); 4.22 (s; 1H); 7.13 (dd; 1H; Jorto=9 Hz and Jmeta=2.56 Hz); 7.26 (d; 1H; Jmeta=2.39 Hz); 7.45 (dd; 1H; Jorto8.53 Hz and Jmeta=1.88 Hz); 7.71 (d; 1H); 7.73 (d; 1H; Jorto=8.53 Hz); 7.77 (d; 1H; Jorto=9 Hz) ppm.The IR spectrum (KBr pellet) was as follows: ν 3296 (N-H), 2956 (C-H, CH2 and CH3), ν 1637 (CO=hydrazide), δ 1604, 1450 (C-Haromatic), ν 1261 (C-O), ν 1213 (-CN) cm-1.
	With hydrazine hydrate In methanol for 6h; Reflux;

	With hydrazine hydrate In ethanol for 2h; Reflux;
	With sulfuryl dichloride; hydrazine hydrate Reflux;

Reference： [1]Current Patent Assignee: UNIVERSIDAE ESTADUAL PAULISTA - EP2418200, 2012, A1 Location in patent: Page/Page column 31
[2]Current Patent Assignee: UNIVERSIDAE ESTADUAL PAULISTA - US2012/115817, 2012, A1 Location in patent: Page/Page column 43
[3]Location in patent: experimental part Parcha, Versha; Kaur, Jaswinder; Gupta, Vinay; Anroop [Journal of the Indian Chemical Society, 2008, vol. 85, # 3, p. 321 - 325]
[4]Aydin, Sevil; Kaushik-Basu, Neerja; Oezbas-Turan, Suna; Akbuga, Juelide; Tiber, Pinar Mega; Orun, Oya; Gurukumar; Basu, Amartya; Kuecuekguezel, S. Gueniz [Letters in drug design and discovery, 2014, vol. 11, # 2, p. 121 - 131]
[5]Li, Zhiyou; Wu, Lamei; Zhang, Tao; Huang, Zhengxi; Qiu, Guofu; Zhou, Zhongqiang; Jin, Longfei [Dalton Transactions, 2014, vol. 43, # 20, p. 7554 - 7560]

43
[ 23981-80-8 ]
[ 18107-18-1 ]
[ 30012-51-2 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol In hexane; benzene at 20℃; for 0.166667h;

Reference： [1]Location in patent: experimental part Noji, Masahiro; Sunahara, Haruka; Tsuchiya, Ken-Ichi; Mukai, Toru; Komasaka, Ayako; Ishii, Keitaro [Synthesis, 2008, # 23, p. 3835 - 3845]

44
[ 30012-51-2 ]
[ 23979-41-1 ]
[ 81623-44-1 ]
[ 26159-35-3 ]

Reference： [1]Advanced Synthesis and Catalysis,2009,vol. 351,p. 2333 - 2341

45
[ 26159-35-3 ]
[ 30012-51-2 ]

Yield	Reaction Conditions	Operation in experiment
97.9%	With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In methanol Reflux;
94%	With n-butyllithium; diisopropylamine; lithium diisopropyl amide In tetrahydrofuran; water at -78℃; for 0.666667h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Kiesewetter, Matthew K.; Scholten, Marc D.; Kirn, Nicole; Weber, Ryan L.; Hedrick, James L.; Waymouth, Robert M. [Journal of Organic Chemistry, 2009, vol. 74, # 24, p. 9490 - 9496]
[2]Burns, Alexander S.; Wagner, Alexander J.; Fulton, Jennifer L.; Young, Kyle; Zakarian, Armen; Rychnovsky, Scott. D. [Organic Letters, 2017, vol. 19, # 11, p. 2953 - 2956]

46
[ 30012-51-2 ]
[ 22204-53-1 ]
[ 81623-44-1 ]

Yield	Reaction Conditions	Operation in experiment
	With Sporopollenin-gel encapsulated Candida rugosa lipase In 2,2,4-trimethylpentane at 30℃; for 24h; aq. phosphate buffer; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;
	With water In 2,2,4-trimethylpentane at 30℃; for 24h; aq. phosphate buffer; Enzymatic reaction; optical yield given as %ee;
	With Fe₃O₄nanoparticle encapsulated on Candida rugosa lipase In aq. buffer at 37℃; Resolution of racemate; Enzymatic reaction; enantioselective reaction;

Reference： [1]Location in patent: experimental part Yilmaz, Elif; Sezgin, Mehmet; Yilmaz, Mustafa [Journal of Molecular Catalysis B: Enzymatic, 2010, vol. 62, # 2, p. 162 - 168]
[2]Location in patent: experimental part Sayin, Serkan; Yilmaz, Elif; Yilmaz, Mustafa [Organic and Biomolecular Chemistry, 2011, vol. 9, # 11, p. 4021 - 4024]
[3]Ozyilmaz, Elif; Bayrakci, Mevlut; Yilmaz, Mustafa [Bioorganic Chemistry, 2016, vol. 65, p. 1 - 8]

47
[ 67-56-1 ]
[ 22204-53-1 ]
[ 30012-51-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sulfuric acid for 6h; Reflux;	3.1 3.1. Synthesis of the intermediary methyl 2- (6-methoxy-2-naftyl) propanoate In a 250 mL flask connected to a reflux condenser there were added 0.7 g (3 mmol) of naproxen, 50 mL of methanol and 2 drops of concentrated sulfuric acid. The reaction is kept under reflux and stirring for 6 hours until thin layer chromatography indicated the completion of the reaction (Mobile phase: 90% dichloromethane; 10% methanol). The product was obtained by removing the solvent at reduced pressure to provide 0.74 g of an orange color solid with melting range between 88° - 94° C (C15H16O3, MW=244.11, yield: 100%). The NMR H1 spectrum (400MHz, DMSOd) was as follows: δ 1.47 (d; 3H); 3.59 (s; 3H); 3.86 (s; 3H); 3.94 (q; 1H); 7.15 (dd; 1H; Jorto=8.7 Hz and Jmeta=2.56 Hz); 7.29 (d; 1H; Jmeta=2.56 Hz); 7.38 (dd; 1H; Jorto=8.53 Hz and Jmeta=1.87 Hz); 7.72 (d; 1H); 7.79 (Jorto= 8.87 Hz; 2H) ppm. The IR spectrum (KBr pellet) was as follows: ν 2976 (C-H, CH2 and CH3) ν 1739.7 (C=O ester), δ 1604, 1450 (C-Haromatic); ν 1267 (C-O) cm-1.
98%	With sulfuric acid for 18h; Reflux;	methyl 2-(6-methoxynaphthalen-2-yl)propanoate (S18). Naproxen (800 mg, 3.47 mmol) wasdissolved in methanol (150 mL) and concentrated sulfuric acid (4 mL) was added and refluxedfor 18 hours. The solution was allowed to cool to room temperature, then washed with water andextracted with dichloromethane. The organic layers were combined, dried over sodium sulfate,filtered, and concentrated to yield S18 (830 mg, 98%) as a white solid.Rf: 0.14 (5% ethyl acetate/hexanes).1H NMR (400 MHz, CDCl3): δ = 7.70 (d, J = 8.5 Hz, 2H, 7.66 (d, J =1.8 Hz, 1H), 7.40 (dd, J =8.5, 1.8 Hz, 1H), 7.16 - 7.10 (m, 2H), 3.91 (s, 3H), 3.86 (q, J = 7.2 Hz, 1H), 3.67 (s, 3H), 1.58 (d,J = 7.2 Hz, 3H)13C NMR (101 MHz, CDCl3): δ = 175.3, 157.8, 135.8, 133.9, 129.4, 129.1, 127.3, 126.3, 126.1,119.1, 105.8, 55.5, 52.2, 45.5, 18.7
93%	Stage #1: (2S)-2-(6-methoxy(2-naphthyl))propanoic acid With sulfuryl dichloride In dichloromethane at 50℃; for 1h; Stage #2: methanol With triethylamine In dichloromethane at 20℃;

Reference： [1]Current Patent Assignee: UNIVERSIDAE ESTADUAL PAULISTA - EP2418200, 2012, A1 Location in patent: Page/Page column 31
[2]Fosu, Stacy C.; Hambira, Chido M.; Chen, Andrew D.; Fuchs, James R.; Nagib, David A. [Chem, 2019, vol. 5, # 2, p. 417 - 428]
[3]Song, Zhi-Qiang; Wang, Dong-Hui [Organic Letters, 2020, vol. 22, # 21, p. 8470 - 8474]

48
[ 30012-51-2 ]
N-(1,3-dioxoisoindolin-2-yl)-2-(6-methoxynaphthalen-2-yl)propanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: hydrazine hydrate / methanol / 24 h / Reflux 2.1: acetic acid / 3 h / 130 °C / Reflux 2.2: pH 7
	Multi-step reaction with 2 steps 1.1: hydrazine hydrate / methanol / 24 h / Reflux 2.1: acetic acid / 3 h / 130 °C 2.2: pH 7 / Cooling

Reference： [1]Current Patent Assignee: UNIVERSIDAE ESTADUAL PAULISTA - EP2418200, 2012, A1
[2]Current Patent Assignee: UNIVERSIDAE ESTADUAL PAULISTA - US2012/115817, 2012, A1

49
[ 30012-51-2 ]
[ 69337-85-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 0.5 h / -78 - 0 °C / Inert atmosphere 1.3: 1 h / 0 - 20 °C / Inert atmosphere 2.1: potassium trimethylsilonate / tetrahydrofuran / 2 h / Reflux

Reference： [1]Windsor, Matthew A.; Hermanson, Daniel J.; Kingsley, Philip J.; Xu, Shu; Crews, Brenda C.; Ho, Winnie; Keenan, Catherine M.; Banerjee, Surajit; Sharkey, Keith A.; Marnett, Lawrence J. [ACS Medicinal Chemistry Letters, 2012, vol. 3, # 9, p. 759 - 763]

50
[ 30012-51-2 ]
[ 105937-62-0 ]

Yield	Reaction Conditions	Operation in experiment
69%	With oxygen; caesium carbonate; triethyl phosphite In dimethyl sulfoxide at 25℃; for 24h; Schlenk technique;

Reference： [1]Liang, Yu-Feng; Jiao, Ning [Angewandte Chemie - International Edition, 2014, vol. 53, # 2, p. 548 - 552][Angew. Chem., 2014, vol. 53, # 2, p. 558 - 562,5]

51
[ 30012-51-2 ]
[ 23979-41-1 ]
[ 81623-44-1 ]

Reference： [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 6634 - 6642

52
[ 63444-51-9 ]
[ 30012-51-2 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 3544 - 3547

53
[ 67-56-1 ]
[ 1058162-97-2 ]
[ 30012-51-2 ]

Yield	Reaction Conditions	Operation in experiment
0.107 g	In toluene at 90℃; for 24h; Sealed tube;

Reference： [1]Ren, Wenlong; Chang, Wenju; Wang, Yang; Li, Jingfu; Shi, Yian [Organic Letters, 2015, vol. 17, # 14, p. 3544 - 3547]

54
[ 30012-51-2 ]
[ 100-51-6 ]
(S)-(phenyl)methyl-2-(6-methoxynaphthalen-2-yl)propanoate [ No CAS ]
(S)-benzyl 2-(6-methoxynaphthalen-2-yl)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With lanthanum(III) nitrate hexahydrate; 1,1,1-trioctyl-1-methylphosphonium methylcarbonate In hexane at 80℃; for 24h; Molecular sieve;	61 General procedure: In Examples 58 to 61, 2 equivalents of an alcohol compound, 3 mol% of lanthanum nitrate hexahydrate, 6 mol% of methyltri-octylphosphonium methyl carbonate, , And the transesterification reaction was carried out under the conditions shown in Table 12. As a result, optically active ester products were obtained in high yield and high enantioselectivity in each case. When methyltridodecylammonium methyl carbonate alone was used in place of lanthanum nitrate hexahydrate and methyltri-octylphosphonium methyl carbonate of Examples 58 to 61 alone, the ester product was obtained in high yield Although it was racemized.

Reference： [1]Current Patent Assignee: TOKAI NATIONAL HIGHER EDUCATION AND RESEARCH SYSTEM - JP5804472, 2015, B2 Location in patent: Paragraph 0085; 0086

55
[ 30012-51-2 ]
(S)-2-(6-methoxynaphthalen-2-yl)propyl propionate [ No CAS ]
(2R)-2-(6-methoxy-naphthalen-2-yl)-propan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / Inert atmosphere 2: 2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine; N-ethyl-N,N-diisopropylamine / chloroform-d1 / 0 °C / Inert atmosphere

Reference： [1]Burns, Alexander S.; Wagner, Alexander J.; Fulton, Jennifer L.; Young, Kyle; Zakarian, Armen; Rychnovsky, Scott. D. [Organic Letters, 2017, vol. 19, # 11, p. 2953 - 2956]

56
[ 30012-51-2 ]
C₁₇H₂₀O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / Inert atmosphere 2: 2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine; N-ethyl-N,N-diisopropylamine / chloroform-d1 / 0 °C / Inert atmosphere 3: 2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine; N-ethyl-N,N-diisopropylamine / chloroform-d1 / 0 °C / Inert atmosphere; Cooling

Reference： [1]Burns, Alexander S.; Wagner, Alexander J.; Fulton, Jennifer L.; Young, Kyle; Zakarian, Armen; Rychnovsky, Scott. D. [Organic Letters, 2017, vol. 19, # 11, p. 2953 - 2956]

57
[ 30012-51-2 ]
[ 292638-85-8 ]
(E)-methyl 3-(7-methoxy-3-(1-methoxy-1-oxopropan-2-yl)naphthalen-2-yl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With (S)-acetamidoalanine; palladium diacetate; silver nitrate at 50℃; for 24h; chemoselective reaction;	2. General procedure and characterization data for products General procedure for the ortho-olefination of aromatic acetyl esters General procedure: In air, a 25 mL sealed tube was charged with aromatic acetyl ester (0.2 mmol, 1 equiv), alkene (0.3 mmol, 1.5 equiv), Pd(OAc)2 (4.5 mg, 10 mol%), Ac-Ala-OH (5.3 mg, 20 mol%), AgNO3 (68 mg, 0.4 mmol, 2 equiv) and HFIP (2 mL). The resulting solution was stirred at 50-80 C under air for 6-24 hours. Upon completion of the reaction, the mixture was cooled down to room temperature and the reaction mixture was diluted with ethyl acetate, filtered through a silica gel plug, rinsed with ethyl acetate, and concentrated in vacuo. The crude reaction mixture was purified on silica gel (petroleum ether: ethyl acetate = 30:1-2:1) to afford the desired product.

Reference： [1]Xiang, Lei; Yang, Kai; Song, Qiu-Ling [Chinese Chemical Letters, 2017, vol. 28, # 3, p. 517 - 520]

58
[ 27607-77-8 ]
[ 30012-51-2 ]
C₁₆H₁₅F₃O₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With [bis(acetoxy)iodo]benzene In dichloromethane at 20℃; for 0.583333h; Inert atmosphere; regioselective reaction;

Reference： [1]Fosu, Stacy C.; Hambira, Chido M.; Chen, Andrew D.; Fuchs, James R.; Nagib, David A. [Chem, 2019, vol. 5, # 2, p. 417 - 428]

59
[ 30012-51-2 ]
[ 36814-90-1 ]

Yield	Reaction Conditions	Operation in experiment
73%	With hydrogenchloride; [bis(acetoxy)iodo]benzene In water; 1,2-dichloro-ethane at 50℃; for 1.5h; regioselective reaction;	methyl 2-(5-chloro-6-methoxynaphthalen-2-yl)propanoate (31). Naproxen methyl ester S18(36.6 mg, 0.15 mmol) was reacted with iodobenzene diacetate (74 mg, 0.23 mmol) and 1Mhydrochloric acid (750 μL, 0.75 mmol) in dichloroethane (1 mL) for 1.5 hours. The crude productwas purified by column chromatography eluting with 10% ethyl acetate/hexanes to yield 31 (30.7mg, 73%) as a white solidRf: 0.14 (5% ethyl acetate/hexanes)mp: 106.3 - 108.0 °C1H NMR (600 MHz, CDCl3): δ = 8.18 (d, J = 8.8 Hz, 1H), 7.74 (d, J = 9.0 Hz, 1H), 7.69 (d, J =1.5 Hz, 1H), 7.53 (dd, J = 8.8, 1.7 Hz, 1H), 7.30 (d, J = 9.0 Hz, 1H), 4.03 (s, 3H), 3.88 (q, J = 7.2Hz, 1H), 3.68 (s, 3H), 1.59 (d, J = 7.2 Hz, 3H)13C NMR (151 MHz, CDCl3): δ = 175.0, 152.8, 136.7, 131.3, 129.7, 128.0, 127.6, 126.3, 124.2,117.1, 114.3, 57.2, 52.2, 45.4, 18.6HRMS (ESI-TOF) m/z: calc’d for C15H15ClO3Na [M+Na]+ 301.0607, found 301.0592IR (film) cm-1: 2976, 2954,1736, 1599, 1331, 1273, 1151, 1066, 881, 798, 526
44%	With hydrogenchloride; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; hydrogen bromide; oxygen In water; acetonitrile at 25℃; for 0.5h; Irradiation; regioselective reaction;

Reference： [1]Fosu, Stacy C.; Hambira, Chido M.; Chen, Andrew D.; Fuchs, James R.; Nagib, David A. [Chem, 2019, vol. 5, # 2, p. 417 - 428]
[2]Düsel, Simon Josef Siegfried; König, Burkhard [European Journal of Organic Chemistry, 2020, vol. 2020, # 10, p. 1491 - 1495]

60
[ 30012-51-2 ]
[ 136945-97-6 ]

Yield	Reaction Conditions	Operation in experiment
68%	With [bis(acetoxy)iodo]benzene; hydrogen bromide In 1,2-dichloro-ethane at 50℃; for 1.5h; regioselective reaction;	methyl 2-(5-chloro-6-methoxynaphthalen-2-yl)propanoate (32). Naproxen methyl ester S18(36.6 mg, 0.15 mmol) was reacted with iodobenzene diacetate (74.1 mg, 0.23 mmol) and 48%hydrobromic acid (102 μL, 0.75 mmol) in dichloroethane (1 mL) for 1.5 hours. The crude productwas purified by column chromatography eluting with 10% ethyl acetate/hexanes to yield 32 (32.8mg, 68%) as a white solid.Rf: 0.06 (5% ethyl acetate/hexanes)mp: 92.7 - 94.3°C1H NMR (400 MHz, CDCl3): δ = 8.18 (d, J = 8.6 Hz, 1H), 7.79 (d, J = 9.0 Hz, 1H), 7.68 (d, J =1.8 Hz, 1H), 7.52 (dd, J = 9.0, 1.8 Hz, 1H), 7.27 (d, J = 8.6 Hz, 1H), 4.03 (s, 3H), 3.87 (q, J = 7.2Hz, 1H), 3.67 (s, 3H), 1.59 (d, J = 7.2 Hz, 1H)13C NMR (151 MHz, CDCl3): δ = 175.0, 153.9, 136.7, 132.5, 130.0, 129.0, 127.8, 126.9, 126.3,114.1, 108.7, 57.2, 52.3, 45.3, 18.6HRMS (ESI-TOF) m/z: calc’d for C15H15BrNaO3 [M+Na]+ 345.0102, found 345.0072IR (film) cm-1: 904, 727, 650
63%	With [bis(acetoxy)iodo]benzene; hydrogen bromide In water; 1,2-dichloro-ethane at 50℃; for 12h; Schlenk technique;

Reference： [1]Fosu, Stacy C.; Hambira, Chido M.; Chen, Andrew D.; Fuchs, James R.; Nagib, David A. [Chem, 2019, vol. 5, # 2, p. 417 - 428]
[2]Song, Zhi-Qiang; Wang, Dong-Hui [Organic Letters, 2020, vol. 22, # 21, p. 8470 - 8474]

61
[ 5111-65-9 ]
Methyl 2-<(methoxallyl)oxy>acetate [ No CAS ]
[ 30012-51-2 ]

Yield	Reaction Conditions	Operation in experiment
70%	With pyridine; nickel(II) iodide; 4,5-dihydro-2-(pyridin-2-yl)-1H-imidazole; magnesium chloride; zinc In N,N-dimethyl acetamide at 20℃; for 12h; Schlenk technique; Inert atmosphere;

Reference： [1]Gao, Mengyu; Sun, Deli; Gong, Hegui [Organic Letters, 2019, vol. 21, # 6, p. 1645 - 1648]

62
[ 30012-51-2 ]
[ 115262-01-6 ]
methyl 3,3-difluoro-2-(6-methoxynaphthalen-2-yl)-2-methylpropanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: methyl 2-(6-methoxy-2-naphthyl)propionate With potassium hexamethylsilazane; sodium t-butanolate In toluene at 0℃; for 0.166667h; Schlenk technique; Glovebox; Inert atmosphere; Stage #2: [bromo(difluoro)methyl]-trimethyl-silane In toluene at 20℃; for 4h; Schlenk technique; Glovebox; Inert atmosphere;

Reference： [1]Xie, Qiqiang; Zhu, Ziyue; Li, Lingchun; Ni, Chuanfa; Hu, Jinbo [Angewandte Chemie - International Edition, 2019, vol. 58, # 19, p. 6405 - 6410][Angew. Chem., 2019, vol. 131, # 19, p. 6471 - 6476,6]

63
[ 67-56-1 ]
[ 23981-48-8 ]
[ 30012-51-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; potassium <i>tert</i>-butylate; 1,2-bis-(diphenylphosphino)ethane at 150℃; for 48h; Inert atmosphere;

Reference： [1]Tsukamoto, Yuya; Itoh, Satoshi; Kobayashi, Masaki; Obora, Yasushi [Organic Letters, 2019, vol. 21, # 9, p. 3299 - 3303]

64
[ 23981-47-7 ]
[ 30012-51-2 ]

Reference： [1]Organic Letters,2019,vol. 21,p. 3299 - 3303

65
[ 30012-51-2 ]
C₁₈H₈Co₂O₈ [ No CAS ]
[ 3453-63-2 ]
methyl 2-(6-methoxy-5-(pro-2-yn-1-yl)naphthalen-2-yl)propanate dicobalt hexacarbonyl [ No CAS ]
C₁₈H₈Co₂O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 64% 2: 51% 3: 29%	With triphenylphosphinogold(I) hexafluoroantimonate In dichloromethane at 20℃; for 0.5h; Molecular sieve; Inert atmosphere;

Reference： [1]Okamura, Toshitaka; Fujiki, Shogo; Iwabuchi, Yoshiharu; Kanoh, Naoki [Organic and Biomolecular Chemistry, 2019, vol. 17, # 37, p. 8522 - 8526]

66
[ 30012-51-2 ]
C₂₄H₁₁Co₂F₉O₈ [ No CAS ]
methyl 2-(6-methoxy-5-(pro-2-yn-1-yl)naphthalen-2-yl)propanate dicobalt hexacarbonyl [ No CAS ]
C₁₅H₉F₉O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 99% 2: 99%	With triphenylphosphinogold(I) hexafluoroantimonate In dichloromethane at 20℃; for 0.5h; Molecular sieve; Inert atmosphere;

Reference： [1]Okamura, Toshitaka; Fujiki, Shogo; Iwabuchi, Yoshiharu; Kanoh, Naoki [Organic and Biomolecular Chemistry, 2019, vol. 17, # 37, p. 8522 - 8526]

67
[ 30012-51-2 ]
C₂₆H₁₁Co₂F₁₃O₈ [ No CAS ]
methyl 2-(6-methoxy-5-(pro-2-yn-1-yl)naphthalen-2-yl)propanate dicobalt hexacarbonyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With C₂₀H₁₂AuF₉NO₄PS₂ In 1,2-dichloro-ethane at 20℃; for 0.25h; Inert atmosphere; Molecular sieve;

Reference： [1]Okamura, Toshitaka; Fujiki, Shogo; Iwabuchi, Yoshiharu; Kanoh, Naoki [Organic and Biomolecular Chemistry, 2019, vol. 17, # 37, p. 8522 - 8526]

68
[ 30012-51-2 ]
C₂₆H₁₁Co₂F₁₃O₈ [ No CAS ]
methyl 2-(6-methoxy-5-(pro-2-yn-1-yl)naphthalen-2-yl)propanate dicobalt hexacarbonyl [ No CAS ]
3-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-1H-isochromen-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 99% 2: 99%	With triphenylphosphinogold(I) hexafluoroantimonate In dichloromethane at 20℃; for 0.5h; Molecular sieve; Inert atmosphere;

Reference： [1]Okamura, Toshitaka; Fujiki, Shogo; Iwabuchi, Yoshiharu; Kanoh, Naoki [Organic and Biomolecular Chemistry, 2019, vol. 17, # 37, p. 8522 - 8526]

69
[ 30012-51-2 ]
C₂₂H₁₆Co₂O₈ [ No CAS ]
[ 30531-69-2 ]
methyl 2-(6-methoxy-5-(pro-2-yn-1-yl)naphthalen-2-yl)propanate dicobalt hexacarbonyl [ No CAS ]
C₂₂H₁₆Co₂O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 74% 2: 78% 3: 19%	With triphenylphosphinogold(I) hexafluoroantimonate In dichloromethane at 20℃; for 0.5h; Molecular sieve; Inert atmosphere;

Reference： [1]Okamura, Toshitaka; Fujiki, Shogo; Iwabuchi, Yoshiharu; Kanoh, Naoki [Organic and Biomolecular Chemistry, 2019, vol. 17, # 37, p. 8522 - 8526]

70
[ 67-56-1 ]
[ 201230-82-2 ]
[ 132367-16-9 ]
[ 136579-95-8 ]
[ 30012-51-2 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; toluene-4-sulfonic acid; bis[2-(diphenylphosphino)phenyl] ether In toluene at 130℃; for 18h; Autoclave; Overall yield = 90 percent; regioselective reaction;

Reference： [1]Beller, Matthias; Jackstell, Ralf; Maes, Bert U. W.; Schneider, Carolin [European Journal of Organic Chemistry, 2020]

71
[ 67-56-1 ]
[ 201230-82-2 ]
[ 63444-51-9 ]
[ 30012-51-2 ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: carbon monoxide; 2-methoxy-6-vinylnapthalene With hydrogenchloride In water for 20h; Schlenk technique; Inert atmosphere; Stage #2: methanol With diazomethyl-trimethyl-silane In water for 2h; Schlenk technique; Inert atmosphere; Reflux;	Experimental procedure for the synthesis of 2-aryl-propionic acids General procedure: In a 100 mL Schlenk vial 0.75 mol% (11.79 mg) Pd(OAc)2, 3.0 mol% (67.7 mg) NIPCDPP 9 weredissolved in 14 mL dioxane and 0.2 eq (410 μL) hexadecane as internal standard was added. Underargon 2.0 mL of this homogeneous yellow stock solution was transferred to each of six 4 mL vialsequipped with a septum, needle and stirring bar, which are placed in an alloy plate. After 1 mmolof the corresponding aryl bromide and 1.5 eq (208 μL) of NEt3 were added to each vial and a smallsample was withdrawn for GC, the alloy plate was transferred into the 300 mL autoclave. Thesealed autoclave was purged with ethylene several times and pressurized with 10 bar ethylene.Then, the reaction was run at 120 °C for 20 h. Afterwards the autoclave was cooled down to roomtemperature and the gas was carefully released. In the vials a grey precipitate were formed and thesolution was still yellow. After a small sample for GC analyses was withdrawn, 83 μL of 6M HCLwas added carefully. The reaction solution foams. Next, the autoclave was flushed with CO threetimes and the reaction was allowed to run at 40 bar CO. After 20 h, the autoclave was cooled downand the gas was released again. In order to determine the yield by GC, a sample of 100 μL of eachreaction solution was esterified with (trimethylsilyl)diazomethane in the presence of 100 μL MeOH.The products were chromatographed after esterification in 10 mL MeOH and one drop cc H2SO4 (2h refluxing) and characterized by NMR, elemental analysis and mass spectroscopy.

Reference： [1]Neumann, Helfried; Sergeev, Alexey G.; Spannenberg, Anke; Beller, Matthias [Molecules, 2020, vol. 25, # 15]

72
[ 30012-51-2 ]
methyl 2-(6-methoxy-5-(p-tolyl)naphthalen-2-yl)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 2,2,2-trifluoroethanol; dichloromethane / 2 h / 0 - 20 °C / Sealed tube; Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium phosphate / acetonitrile / 12 h / 20 °C / Molecular sieve; Inert atmosphere; Sealed tube