Name: 940-31-8|2-Phenoxypropanoic acid|98%
Brand: Ambeed
SKU: A160032
Price: 8.0 USD
Availability: InStock
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1
[ 940-31-8 ]
[ 122-35-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	In thionyl chloride	3 Phenoxypropionyl chloride EXAMPLE 3 Phenoxypropionyl chloride Phenoxypropionic acid (249.0 g, 1.50 mol) is dissolved in four equivalents of thionyl chloride (438.0 ml, 6.0 mol) and heated to reflux until the HCl evolution has ceased. The solution is then cooled to room temperature and concentrated under reduced pressure to give 281.0 g (100% yield) of phenoxypropionyl chloride as a brown oil which solidifies on cooling. IR (KBr) cm-1: 1793 (C=O); 1 H nmr (CDCl3) δ: 7.31 (m, 2H, phenyl-H), 7.01 (t, 1H, J=7.5 Hz, phenyl-H), 6.92 (m, 2H, phenyl-H), 4.29 (t, 2H. J=5.9 Hz, OCH2), 3.36 (t, 2H, J=5.9 Hz, COCH2); 13 C nmr (CDCl3) δ: 171.9, 158.0, 129.6(2C), 121.6, 114.7(2C), 62.6, 46.7.
96%	With thionyl chloride In N,N-dimethyl-formamide Heating;
94%	With thionyl chloride for 3h; Heating;

94.5%	With thionyl chloride In dichloromethane at 30℃; for 6h;	1 Example 1 In a 2 L reaction flask, 214 g of sodium hydroxide was dissolved with 530 ml of water, 200 g of phenol and 280 g of 2-chloropropionic acid were added, and the reaction was complete at 65° C. with stirring for 6 h. Acidification was adjusted to pH=4 and filtration was performed to obtain an off-white solid powder a. Purity 99.8%, yield 80.3%. Put 205g of white solid powder a into a 2L reaction flask, add 400ml of dichloromethane and 240g of thionyl chloride and stir at 30°C for 6h. The reaction is complete. The organic solvent is removed under reduced pressure at a lower temperature, and the 80°C fraction is collected to obtain light Yellow oily liquid b, purity 98.24%, yield 94.5%.
24%	With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 20℃; Inert atmosphere;
	With phosphorus pentachloride at 80 - 90℃;
	With thionyl chloride In ethyl acetate; benzene for 8h; Heating;
5 g	With thionyl chloride Ambient temperature;
	With thionyl chloride In methanol; ethyl acetate for 7h; Heating;
	With thionyl chloride for 1h; Heating;
	With thionyl chloride at 50℃;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h;
	With thionyl chloride
	With thionyl chloride In dichloromethane at 20℃; for 3h; Inert atmosphere; Schlenk technique; Reflux;
	With phosphorus pentachloride In benzene at 60℃; for 1h;	General procedure for the preparation of compounds 1-4 General procedure: To a solution of the corresponding DL-2-phenoxypropionic acid (6.02 mmol) in anhydrous benzene (40 mL) was added phosphorous pentachloride (9.62 mmol) and stirred at 60 °C for 1 h. Evaporation of the solvent gave acid chloride which was washed with anhydrous benzene. This acid chloride was dissolved in anhydrous benzene (40 mL) and added to a solution of methyl anthranilate (5.42 mmol) in benzene (20 mL) and then the reaction mixture was stirred at room temperature for 12 h. The reaction mixture was added with water, extracted with ethyl acetate and the organic extracts were dried with anhydrous MgSO4 and filtered. The filtrate was concentrated to yield crude precipitate which was recrystallized with ethyl acetate and n-hexane to afford 1-4 as a white powder.
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 3h;	General synthetic procedure for compounds 8-11 and 13-36 General procedure: To a stirred suspension of various carboxylic acid 4a, 4b, 6a and 8a (1.0 equiv) in CH2Cl2 (25 mL) was added oxalyl chloride (3.0 equiv) and a catalytic amount of DMF. After stirring at room temperature for 3 h, the reaction was concentrated under reduced pressure to afford a yellow oil crude acyl chloride. To a solution of methyl 2-(4-amino-2-fluorophenoxy)acetate 3a (1.0 equiv) in CH2Cl2(25 mL) was added Et3N (1.5 equiv), and this mixture was cooled to -5 °C. Subsequently, the crude acyl chloride obtained above was added in dropwise at a rate to ensure that the temperature did not exceed 0 °C. The solution was stirred for another 2 hrs at 25 °C, then washed successively with 10% HCl (2 × 25 mL), 10% NaHCO3 (2 × 25 mL) and brine (2 × 20 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and the solvent was then evaporated to give the impure amide which was recrystallized from ethanol to give the desired products as colorless crystals. To a solution of the obtained crystals (1.0 equiv)in 2:3:1 THF/MeOH/H2O (18 ml) was added LiOH·H2O (1.5 equiv). After stirring at room temperature for 4 h, the volatiles were removed under reduced pressure. The residue was acidified with 1N hydrochloric acid solution, and then filtered and the filter cake was washed with 5 mL of water, dried in vacuum to afford a white powder. Recrystallization from 75% EtOH gave the desired compounds 8-11 and 13-36 as colorless crystals.
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 6h; Inert atmosphere;

Reference： [1]Current Patent Assignee: APOTEX INC - US5900485, 1999, A
[2]Heathcock,C.H.; Pirrung,M.C.; Young,S.D. [Journal of the American Chemical Society, 1984, vol. 106, p. 8161]
[3]Salz, Ulrich; Ruechardt, Christoph [Chemische Berichte, 1984, vol. 117, # 12, p. 3457 - 3462]
[4]Current Patent Assignee: ENANTIOTECH - CN107827734, 2018, A Location in patent: Paragraph 0030
[5]Location in patent: experimental part Markovic, Bojan; Vladimirov, Sote; Cudina, Olivera; Savic, Vladimir; Karljikovic-Rajic, Katarina [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2010, vol. 75, # 2, p. 930 - 935]
[6]Bischoff [Chemische Berichte, 1901, vol. 34, p. 1839]
[7]Jain; Srivastava [Journal of the Indian Chemical Society, 1990, vol. 67, # 9, p. 775 - 776]
[8]Sharma; Rani; Talwar; Kalsi [Journal of the Indian Chemical Society, 1991, vol. 68, # 3, p. 135 - 137]
[9]Purohit; Srivastava [Journal of the Indian Chemical Society, 1991, vol. 68, # 3, p. 163 - 165]
[10]Gualtieri; Bottalico; Calandrella; Dei; Giovannoni; Mealli; Romanelli; Scapecchi; Teodori; Galeotti; Ghelardini; Giotti; Bartolini [Journal of Medicinal Chemistry, 1994, vol. 37, # 11, p. 1712 - 1719]
[11]Plazek et al. [Roczniki Chemii, 1935, vol. 15, p. 365,370][Chemisches Zentralblatt, 1936, vol. 107, # I, p. 1219]
[12]Zhang, Kai; Peng, Qian; Hou, Xue-Long; Wu, Yun-Dong [Angewandte Chemie - International Edition, 2008, vol. 47, # 9, p. 1741 - 1744]
[13]Zhai, Weixu; Flynn, Neil; Longhi, Daniel A.; Tino, Joseph A.; Murphy, Brian J.; Slusarchyk, Dorothy; Gordon, David A.; Pendri, Anna; Shi, Shuhao; Stoffel, Robert; Ma, Baoqing; Sofia, Michael J.; Gerritz, Samuel W. [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 18, p. 5083 - 5086]
[14]Location in patent: body text Markovic, Bojan D.; Dobricic, Vladimir D.; Vladimirov, Sote M.; Cudina, Olivera A.; Savic, Vladimir M.; Karljikovic-Rajic, Katarina D. [Molecules, 2011, vol. 16, # 3, p. 2658 - 2671]
[15]John, Jeremy M.; Takebayashi, Satoshi; Dabral, Nupur; Miskolzie, Mark; Bergens, Steven H. [Journal of the American Chemical Society, 2013, vol. 135, # 23, p. 8578 - 8584]
[16]Kim, Sohee; Shin, Beom Soo; Ma, Eunsook [Archives of Pharmacal Research, 2015, vol. 38, # 6, p. 1147 - 1156]
[17]Li, Zheng; Wang, Xuekun; Xu, Xue; Yang, Jianyong; Qiu, Qianqian; Qiang, Hao; Huang, Wenlong; Qian, Hai [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 20, p. 6666 - 6672]
[18]Korolyova, Marina A.; Vakarov, Sergey A.; Kozhevnikov, Dmitry N.; Gruzdev, Dmitry A.; Levit, Galina L.; Krasnov, Victor P. [European Journal of Organic Chemistry, 2018, vol. 2018, # 33, p. 4577 - 4585]

2
[ 42412-84-0 ]
[ 940-31-8 ]

Yield	Reaction Conditions	Operation in experiment
73.3%	With water; sodium hydroxide In ethanol at 25℃; for 0.5h;	19.2 Step 2: 2-phenoxypropanoic acid To a solution of ethyl 2-phenoxypropanoate (1.8 g, 0.9 mmol) in EtOH (16 ml) was added a solution of NaOH (0.44 g, 1.1 mmol) in H20 (4 ml) at 25 °C . The mixture was stirred for 30 min before being concentrated. The residue had water (20 mL) added and washed with ethyl acetate (2x20 mL). The aqueous layer was acidified with 2N HCL until pH 3 and extracted with ethyl acetate (2x20 mL). The combined organic layers were washed with brine (30 mL), dried over Na2S04 and concentrated to give the title compound (1.1 g, 73.3%) as a white solid which was used in next step without further purification.
73.3%	With water; sodium hydroxide In ethanol at 25℃; for 0.5h;	19.2 Step 2: 2-phenoxypropanoic Acid To a solution of 101 ethyl 2-phenoxypropanoate (1.8 g, 0.9 mmol) in 8 EtOH (16 ml) was added a solution of 42 NaOH (0.44 g, 1.1 mmol) in 92 H2O (4 ml) at 25° C. The mixture was stirred for 30 min before being concentrated. The residue had 43 water (20 mL) added and washed with ethyl acetate (2×20 mL). The aqueous layer was acidified with 2N HCL until pH 3 and extracted with ethyl acetate (2×20 mL). The combined organic layers were washed with brine (30 mL), dried over Na2SO4 and concentrated to give the 103 title compound (1.1 g, 73.3%) as a white solid which was used in next step without further purification.
	With potassium hydroxide

	With alkali Ambient temperature;
	With sodium hydroxide In water Heating;
	With water; sodium hydroxide In tetrahydrofuran at 80℃; for 3h; Inert atmosphere;

Reference： [1]Current Patent Assignee: EPIZYME, INC. - WO2014/100730, 2014, A1 Location in patent: Paragraph 00275
[2]Current Patent Assignee: EPIZYME, INC. - US2019/83482, 2019, A1 Location in patent: Paragraph 0267-0268
[3]Bischoff [Chemische Berichte, 1900, vol. 33, p. 930]
[4]Azzolina; Collina; Ghislandi [Il Farmaco, 1993, vol. 48, # 10, p. 1401 - 1416]
[5]Al-Awadi, Nouria A.; Kaul, Kamini; El-Dusouqui, Osman M. E. [Journal of Physical Organic Chemistry, 2000, vol. 13, # 9, p. 499 - 504]
[6]Gorla, Suresh Kumar; Kavitha, Mandapati; Zhang, Minjia; Chin, James En Wai; Liu, Xiaoping; Striepen, Boris; Makowska-Grzyska, Magdalena; Kim, Youngchang; Joachimiak, Andrzej; Hedstrom, Lizbeth; Cuny, Gregory D. [Journal of Medicinal Chemistry, 2013, vol. 56, # 10, p. 4028 - 4043]

3
[ 940-31-8 ]
[ 120-36-5 ]

Reference： [1]Journal of Organic Chemistry,1947,vol. 12,p. 435
Journal of Organic Chemistry,1948,vol. 13,p. 937

4
[ 940-31-8 ]
[ 62-53-3 ]
[ 101089-96-7 ]

Yield	Reaction Conditions	Operation in experiment
89%	With Candida antarctica lipase immobilized on acrylic resin In n-heptane at 80℃; for 72h; Molecular sieve; Green chemistry; Enzymatic reaction;	Enzymatic amidation of non-activated carboxylic acids General procedure: To a solution of 2 mmol amine and the 1 mmol carboxylic acid dissolved in 1 mL of heptane, 50 mg of the molecular sieves 4 and 50 mg of the immobilized CAL-B are introduced.The reaction mixture is stirred at 80 °C for 72 h. After cooling, the solvent is evaporated and the crude residue was exposed to a standard acido-basic treatment (HCl, 3 M / 3 M NaOH). The solvent was removed in vacuo, and the residue was crystallized in hexane, or purified by flash chromatography if necessary. As a control reaction, the same procedure is followed without introducing lipase. All the synthesized amides are characterized by 1H NMR, 13C NMR spectra and HRMS. Melting points were determined. Separation conditions on chiral HPLC were established. Optical rotations of proline amides 4a-5e were measured.
	at 150℃;

Reference： [1]Benamara, Nourelhouda; Merabet-Khelassi, Mounia; Aribi-Zouioueche, Louisa; Riant, Olivier [Chemical Papers, 2021, vol. 75, # 8, p. 4045 - 4053]
[2]Lambling [Bulletin de la Societe Chimique de France, 1897, vol. <3>17, p. 357]

5
[ 598-72-1 ]
[ 108-95-2 ]
[ 940-31-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; ethanol
	With sodium hydroxide In ethanol for 24h; Heating;
	With base

With sodium hydroxide In ethanol for 24h; Schlenk technique; Inert atmosphere; Reflux;

Reference： [1]Fredga; Matell [Arkiv foer Kemi, 1952, vol. 4, p. 325,326]
[2]Gualtieri; Bottalico; Calandrella; Dei; Giovannoni; Mealli; Romanelli; Scapecchi; Teodori; Galeotti; Ghelardini; Giotti; Bartolini [Journal of Medicinal Chemistry, 1994, vol. 37, # 11, p. 1712 - 1719]
[3]Yang, Xing; Birman, Vladimir B. [Chemistry - A European Journal, 2011, vol. 17, # 40, p. 11296 - 11304]
[4]Liu, Bin; Song, Runjiang; Xu, Jun; Majhi, Pankaj Kumar; Yang, Xing; Yang, Song; Jin, Zhichao; Chi, Yonggui Robin [Organic Letters, 2020, vol. 22, # 9, p. 3335 - 3338]

6
[ 67-56-1 ]
[ 940-31-8 ]
[ 2065-24-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With tert.-butylnitrite at 40℃; for 48h;	43 Add compound 1aq (0.5 mmol, 83.1 mg) and methanol containing 40 mol% tert-butyl nitrite to the reaction tube; then react for 48 hours at 40°C in air; after the reaction, add sodium thiosulfate and stir. After quenching, using a rotary evaporator to remove the solvent, adsorbing on silica gel, and finally performing column chromatography with a mixed solvent of ethyl acetate and petroleum ether to obtain the product 3aq with a yield of 90%.
90%	With tert.-butylnitrite at 40℃; for 48h; Green chemistry;
	With pyridine; O-phenyl phosphorodichloridate

	With boron trifluoride
	With toluene-4-sulfonic acid; 2,2-dimethoxy-propane at 55℃; for 4h;

Reference： [1]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN112552171, 2021, A Location in patent: Paragraph 0065-0066
[2]Cheng, Xionglve; Jiang, Gangzhong; Li, Xingxing; Tao, Suyan; Wan, Xiaobing; Zhao, Yanwei; Zheng, Yonggao [European Journal of Organic Chemistry, 2021, vol. 2021, # 18, p. 2713 - 2718]
[3]Liu,H.-J. et al. [Tetrahedron Letters, 1978, # 46, p. 4461 - 4464]
[4]Redman,R.P. et al. [Journal of the Chemical Society. Perkin transactions II, 1978, p. 1135 - 1144]
[5]Chenevert, Robert; D'Astous, Linda [Canadian Journal of Chemistry, 1988, vol. 66, p. 1219 - 1222]

7
[ 940-31-8 ]
[ 4169-04-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium tetrahydroborate; titanium tetrachloride In 1,2-dimethoxyethane for 14h; Ambient temperature;
92%	With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0 - 20℃;
87%	With hydrogen In neat (no solvent) at 160℃; for 24h;

81%	With borane In tetrahydrofuran at 20℃;
75%	With lithium aluminium tetrahydride In diethyl ether for 3.5h; Heating;
	With lithium aluminium tetrahydride In diethyl ether
70 % Spectr.	With diphenylsilane; triphenylphosphine In tetrahydrofuran at 20℃; for 48h;
	Multi-step reaction with 2 steps 1: BF₃ 2: LiAlH₄
		10 2-Phenoxypropanol PREPARATION 10 2-Phenoxypropanol The title compound was prepared by the procedure of Preparation 2 in quantitative yield from 2-phenoxypropionic acid (Aldrich Chem. Co.) and lithium aluminum hydride.
		12 Preparation 12 Preparation 12 2-Phenoxypropanol. The title compound was prepared by the procedure of Preparation 2 in quantitative yield from 2-phenoxypropionic acid (Aldrich Chem. Co.) and lithium aluminum hydride.

Reference： [1]Kano, Shinzo; Tanaka, Yasuyuki; Sugino, Eiichi; Hibino, Sstoshi [Synthesis, 1980, # 9, p. 695 - 697]
[2]Location in patent: experimental part Ling, Kenneth B.; Smith, Andrew D. [Chemical Communications, 2011, vol. 47, # 1, p. 373 - 375]
[3]Toyao, Takashi; Siddiki, S. M. A. Hakim; Touchy, Abeda S.; Onodera, Wataru; Kon, Kenichi; Morita, Yoshitsugu; Kamachi, Takashi; Yoshizawa, Kazunari; Shimizu, Ken-Ichi [Chemistry - A European Journal, 2017, vol. 23, # 5, p. 1001 - 1006]
[4]Miyazawa, Toshifumi; Yukawa, Tomoyuki; Koshiba, Takashi; Sakamoto, Hiroko; Ueji, Shinichi; Yanagihara, Ryoji; Yamada, Takashi [Tetrahedron Asymmetry, 2001, vol. 12, # 11, p. 1595 - 1602]
[5]Al-Awadi, Nouria A.; Kaul, Kamini; El-Dusouqui, Osman M. E. [Journal of Physical Organic Chemistry, 2000, vol. 13, # 9, p. 499 - 504]
[6]Eliel,E.L. et al. [Journal of the American Chemical Society, 1962, vol. 84, p. 2371 - 2377]
[7]Ohta, Tetsuo; Kamiya, Masahiro; Nobutomo, Mami; Kusui, Keisuke; Furukawa, Isao [Bulletin of the Chemical Society of Japan, 2005, vol. 78, # 10, p. 1856 - 1861]
[8]Redman,R.P. et al. [Journal of the Chemical Society. Perkin transactions II, 1978, p. 1135 - 1144]
[9]Current Patent Assignee: PFIZER INC - US5192785, 1993, A
[10]Current Patent Assignee: PFIZER INC - US5194446, 1993, A

8
[ 109-79-5 ]
[ 940-31-8 ]
[ 62170-11-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With pyridine; O-phenyl phosphorodichloridate In 1,2-dimethoxyethane for 16h; Ambient temperature;

Reference： [1]Liu, Hsing-Jang; Sabesan, Subramaniam Iyer [Canadian Journal of Chemistry, 1980, vol. 58, p. 2645 - 2648]

9
[ 940-31-8 ]
[ 27854-88-2 ]
2-Phenoxy-propionic acid (R)-1-pyridin-4-yl-ethyl ester [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,1992,vol. 3,p. 1455 - 1466

10
[ 940-31-8 ]
[ 1129-46-0 ]
[ 87860-35-3 ]

Reference： [1]Agricultural and Biological Chemistry,1984,vol. 48,p. 1373 - 1374

11
[ 940-31-8 ]
[ 56674-68-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	With hydrogen In acetic acid for 3h; Ambient temperature;

Reference： [1]Ogawa; Terada; Muranaka; Hamakawa; Fujii [Chemical and Pharmaceutical Bulletin, 1987, vol. 35, # 6, p. 2426 - 2436]

12
[ 940-31-8 ]
[ 75-66-1 ]
[ 29279-27-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With pyridine; O-phenyl phosphorodichloridate In 1,2-dimethoxyethane for 16h; Ambient temperature;
	(i) Me₂NPOCl₂, Et₃N, (ii) /BRN= 505947/; Multistep reaction;

Reference： [1]Liu, Hsing-Jang; Sabesan, Subramaniam Iyer [Canadian Journal of Chemistry, 1980, vol. 58, p. 2645 - 2648]
[2]Liu,H.-J. et al. [Synthetic Communications, 1979, vol. 9, p. 91 - 96]

13
[ 940-31-8 ]
[ 122-35-0 ]
[ 446878-78-0 ]

Yield	Reaction Conditions	Operation in experiment
86%	In pyridine; diethyl ether at 25℃; for 3h;

Reference： [1]Salz, Ulrich; Ruechardt, Christoph [Chemische Berichte, 1984, vol. 117, # 12, p. 3457 - 3462]

14
2-phenoxypropanoic acid sodium salt [ No CAS ]
[ 940-31-8 ]

Yield	Reaction Conditions	Operation in experiment
70%	With phosphoric acid

Reference： [1]Heathcock,C.H.; Pirrung,M.C.; Young,S.D. [Journal of the American Chemical Society, 1984, vol. 106, p. 8161]

15
[ 598-78-7 ]
[ 108-95-2 ]
[ 940-31-8 ]

Yield	Reaction Conditions	Operation in experiment
80.3%	With sodium hydroxide In water at 65℃; for 6h;	1 Example 1 In a 2 L reaction flask, 214 g of sodium hydroxide was dissolved with 530 ml of water, 200 g of phenol and 280 g of 2-chloropropionic acid were added, and the reaction was complete at 65° C. with stirring for 6 h. Acidification was adjusted to pH=4 and filtration was performed to obtain an off-white solid powder a. Purity 99.8%, yield 80.3%. Put 205g of white solid powder a into a 2L reaction flask, add 400ml of dichloromethane and 240g of thionyl chloride and stir at 30°C for 6h. The reaction is complete. The organic solvent is removed under reduced pressure at a lower temperature, and the 80°C fraction is collected to obtain light Yellow oily liquid b, purity 98.24%, yield 94.5%.
	With sodium hydroxide In water Heating;
	With sodium hydroxide In water for 20h; Heating;

Reference： [1]Current Patent Assignee: ENANTIOTECH - CN107827734, 2018, A Location in patent: Paragraph 0030; 0031
[2]Purohit; Srivastava [Journal of the Indian Chemical Society, 1991, vol. 68, # 3, p. 163 - 165]
[3]Segurado, Manuel A. P.; Reis, Joao Carlos R.; De Oliveira, Jaime D. Gomes; Kabilan, Senthamaraikannan; Shanthi, Manohar [Journal of Organic Chemistry, 2007, vol. 72, # 14, p. 5327 - 5336]

16
[ 940-31-8 ]
[ 1129-46-0 ]
[ 1912-23-8 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1995,p. 301 - 302
[2]Russian Chemical Bulletin,2021,vol. 70,p. 900 - 907
Izv. Akad. Nauk, Ser. Khim.,2021,p. 900 - 907
[3]Chirality,2022

17
[ 940-31-8 ]
[ 7553-56-2 ]
[ 64-19-7 ]
2 mol chlorine [ No CAS ]
[ 120-36-5 ]

Reference： [1]Journal of Organic Chemistry,1947,vol. 12,p. 435
Journal of Organic Chemistry,1948,vol. 13,p. 937

18
[ 940-31-8 ]
[ 1129-46-0 ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 7234 - 7242
[2]Organic letters,2002,vol. 4,p. 371 - 373
[3]Tetrahedron Letters,1999,vol. 40,p. 2307 - 2310

19
[ 940-31-8 ]
[ 71-36-3 ]
[ 1129-46-0 ]
[ 1912-23-8 ]
(R)-2-Phenoxy-propionic acid butyl ester [ No CAS ]
(S)-2-Phenoxy-propionic acid butyl ester [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,2003,vol. 76,p. 399 - 403

20
[ 940-31-8 ]
[ 252002-18-9 ]
C₂₅H₃₂N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-phenoxypropionic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In chloroform at 20℃; for 0.0833333h; Stage #2: 3-spiro[2,3-dihydro-1H-indene-1,4'-piperidine]-1-ylpropane-1-amine In chloroform at 20℃; for 0.5h;

Reference： [1]Goto, Yasuhiro; Arai-Otsuki, Sachie; Tachibana, Yukari; Ichikawa, Daisuke; Ozaki, Satoshi; Takahashi, Hiroyuki; Iwasawa, Yoshikazu; Okamoto, Osamu; Okuda, Shoki; Ohta, Hisashi; Sagara, Takeshi [Journal of Medicinal Chemistry, 2006, vol. 49, # 3, p. 847 - 849]

21
[ 771-61-9 ]
[ 940-31-8 ]
pentafluorophenyl 2-phenoxypropionate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 1h;	Supplemental experimental procedure A for the synthesis of pentafluorophenyl esters General procedure: Acid (1.228 g, 5.5 mmol) was dissolved in dry THF (15 ml) and cooled to 0 °C. PFP(Pentafluorophenol, 1.114 g, 6.05 mmol) was added dropwise to the solution, at which point a whiteprecipitate formed. DCC (dicyclohexylcarbodiimide, 1.248 g, 6.05 mmol) was added to the solutionand the solution was allowed to stir at 0 °C for 1 h. The white precipitate (DCU) was removed byfiltration, the THF supernatant evaporated and the resulting organic product purified by silica gelcolumn chromatography (hexane: EtOAc).
64%	With dicyclohexyl-carbodiimide In dichloromethane for 12h;

Reference： [1]Flavell, Robert R.; Liu, Jianbo; Parker, Matthew F. L.; Toste, F. Dean; Wang, Sinan; Wilson, David M. [Chem, 2021, vol. 7, # 8, p. 2245 - 2255]
[2]Boyd, Ewan; Chavda, Sameer; Eames, Jason; Yohannes, Yonas [Tetrahedron Asymmetry, 2007, vol. 18, # 4, p. 476 - 482]

22
[ 940-31-8 ]
[ 115880-50-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Nocardia diaphanozonaria cells; glycerol; peptone / beef extract; yeast extract / H₂O / 72 h / 30 °C / pH 7.0
	Multi-step reaction with 2 steps 1: Nocardia diaphanozonaria JCM 3208 / 72 h / 30 °C
	Multi-step reaction with 2 steps 1: p-toluenesulfonic acid, 2,2-dimethoxypropane / 4 h / 55 °C

Reference： [1]Kato, Dai-Ichiro; Mitsuda, Satoshi; Ohta, Hiromichi [Journal of Organic Chemistry, 2003, vol. 68, # 19, p. 7234 - 7242]
[2]Kato, Dai-ichiro; Mitsuda, Satoshi; Ohta, Hiromichi [Organic letters, 2002, vol. 4, # 3, p. 371 - 373]
[3]Chenevert, Robert; D'Astous, Linda [Canadian Journal of Chemistry, 1988, vol. 66, p. 1219 - 1222]

23
[ 940-31-8 ]
[ 92817-69-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 96 percent / SOCl₂ / dimethylformamide / Heating 2: 38 percent / tetrahydrofuran

Reference： [1]Heathcock,C.H.; Pirrung,M.C.; Young,S.D. [Journal of the American Chemical Society, 1984, vol. 106, p. 8161]

24
[ 940-31-8 ]
[ 92817-77-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 96 percent / SOCl₂ / dimethylformamide / Heating 2: 38 percent / tetrahydrofuran 3: LDA / tetrahydrofuran / 0.5 h / -78 °C

Reference： [1]Heathcock,C.H.; Pirrung,M.C.; Young,S.D. [Journal of the American Chemical Society, 1984, vol. 106, p. 8161]

25
[ 940-31-8 ]
[ 92817-75-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 96 percent / SOCl₂ / dimethylformamide / Heating 2: 38 percent / tetrahydrofuran 3: LDA / tetrahydrofuran / 0.5 h / -78 °C

Reference： [1]Heathcock,C.H.; Pirrung,M.C.; Young,S.D. [Journal of the American Chemical Society, 1984, vol. 106, p. 8161]

26
[ 940-31-8 ]
[ 92817-72-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 96 percent / SOCl₂ / dimethylformamide / Heating 2: 38 percent / tetrahydrofuran 3: LDA / tetrahydrofuran / 0.17 h / -78 °C

Reference： [1]Heathcock,C.H.; Pirrung,M.C.; Young,S.D. [Journal of the American Chemical Society, 1984, vol. 106, p. 8161]

27
[ 940-31-8 ]
[ 92817-71-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 96 percent / SOCl₂ / dimethylformamide / Heating 2: 38 percent / tetrahydrofuran 3: LDA / tetrahydrofuran / 0.17 h / -78 °C

Reference： [1]Heathcock,C.H.; Pirrung,M.C.; Young,S.D. [Journal of the American Chemical Society, 1984, vol. 106, p. 8161]

28
[ 940-31-8 ]
[ 92817-78-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 96 percent / SOCl₂ / dimethylformamide / Heating 2: 38 percent / tetrahydrofuran 3: LDA / tetrahydrofuran / 0.5 h / -78 °C

Reference： [1]Heathcock,C.H.; Pirrung,M.C.; Young,S.D. [Journal of the American Chemical Society, 1984, vol. 106, p. 8161]

29
[ 940-31-8 ]
[ 92817-76-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 96 percent / SOCl₂ / dimethylformamide / Heating 2: 38 percent / tetrahydrofuran 3: LDA / tetrahydrofuran / 0.5 h / -78 °C

Reference： [1]Heathcock,C.H.; Pirrung,M.C.; Young,S.D. [Journal of the American Chemical Society, 1984, vol. 106, p. 8161]

30
[ 108-95-2 ]
[ 940-31-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 70 percent / NaH, HMPT / tetrahydrofuran / Ambient temperature 2: 70 percent / 85percent H₃PO₄

Reference： [1]Heathcock,C.H.; Pirrung,M.C.; Young,S.D. [Journal of the American Chemical Society, 1984, vol. 106, p. 8161]

31
[ 940-31-8 ]
[ 446878-78-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	With dicyclohexyl-carbodiimide In dichloromethane stereospecific reaction;
	Multi-step reaction with 2 steps 1: 94 percent / Thionylchlorid / 3 h / Heating 2: 86 percent / pyridine; diethyl ether / 3 h / 25 °C
	With dicyclohexyl-carbodiimide In toluene at 20℃; for 0.25h;

Reference： [1]Location in patent: body text Coulbeck, Elliot; Eames, Jason [Tetrahedron Asymmetry, 2009, vol. 20, # 5, p. 635 - 640]
[2]Salz, Ulrich; Ruechardt, Christoph [Chemische Berichte, 1984, vol. 117, # 12, p. 3457 - 3462]
[3]Yang, Xing; Birman, Vladimir B. [Advanced Synthesis and Catalysis, 2009, vol. 351, # 14-15, p. 2301 - 2304]

32
[ 940-31-8 ]
[ 21744-83-2 ]

Reference： [1]Chemische Berichte,1900,vol. 33,p. 930

33
[ 940-31-8 ]
[ 90676-99-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: LiAlH₄ / diethyl ether 2: H₂ / Rh-Al₂O₃ / ethanol

Reference： [1]Eliel,E.L. et al. [Journal of the American Chemical Society, 1962, vol. 84, p. 2371 - 2377]

34
[ 7428-91-3 ]
[ 940-31-8 ]
C₂₁H₁₇NO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Following the procedure of Example 3 using 2-aminodibenzthiophene (Bull. Soc. Chim. Fr. (1996), 133 (6), 597-610) and the appropriate acid the following compounds were prepared.

Reference： [1]Patent: US2003/225097,2003,A1 .Location in patent: Page 24

35
[ 940-31-8 ]
[ 119-80-2 ]
2[(9-oxo-9H-thioxanthen-2-yl)oxy]-propionic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56.37%	With sulfuric acid at 10 - 40℃; for 4 - 5h;	7 Example 7; Preparation of 2-(2-methyl)-carboxymethoxythioxanthone Concentrated sulphuric acid (120 mls) and dithiobisbenzoic acid (12.2 g) were charged to a reactor and 2-phenoxypropionic acid (23.3 g) was added over 1 to 2 hours at 10° to 15°C with cooling. After stirring for a further 1 hour at 10° to 20°C, then at 30° to 40°C for 2 hours a deep red solution was obtained. This reaction mixture was then quenched onto water (250 mls) whilst allowing the temperature to rise to ∼80°C. The quenched mixture was stirred for a further 25 minutes at ∼80°C then cooled to 30°C. The product precipitated as an oily mass which was slurried in a mixture of water (80 mls), acetic acid (30 mls), and 2-butanone (40 mls) at reflux for 30 minutes, cooled to ambient temperature and filtered. The damp product cake was washed with a mixture of water and 2-butanone followed by water, then dried. 2-(2-Methyl)-carboxymethoxythioxanthone (13.6g) was obtained in 56.37% yield. This was a green powder, melting point = 174° to 177°C.

Reference： [1]Current Patent Assignee: LANXESS AG - EP1380580, 2004, A1 Location in patent: Page 7

36
[ 940-31-8 ]
[ 56222-08-3 ]
[ 868783-51-1 ]

Reference： [1]Patent: JP2005/314407,2005,A .Location in patent: Page/Page column 56

37
3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)]-1H-indazole-3-yl}phenylamine [ No CAS ]
1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (EDCI) [ No CAS ]
[ 940-31-8 ]
N-(3-{1-Perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)](1H-indazol-3-yl)}phenyl)-2-phenoxypropanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane	299.A A. A. N-(3-{1-Perhydro-2H-Pyran-2-Yl-5-[1-(Triphenylmethyl)(1,2,4-Triazol-3-Yl)](1H-Indazol-3-Yl)Phenyl)-2-Phenoxypropanamide To a solution of 2-phenoxypropanoic acid (0.045 g, 0.274 mmol) in 2.5 mL of dichloromethane was added 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (EDCI) (0.057 g, 0.298 mmol). The reaction was stirred at room temperature for 10 min before 3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)]-1H-indazol-3-yl}phenylamine (0.150 g, 0.248 mmol) dissolved in 1 mL of dichloromethane, was added to the solution. The reaction was stirred at room temperature for 3 hours. The reaction mixture was then partitioned between water and dichloromethane. The crude material that was obtained from evaporation of the extracts was not purified further. (Yield not calculated) ES-MS (m/z) 751 [M+H]+.
	In dichloromethane	299.A A. A. N-(3-{1-Perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)((1,2,4-triazol-3-yl)](1H-indazol-3-yl)}phenyl)-2-phenoxypropanamide To a solution of 2-phenoxypropanoic acid (0.045 g, 0.274 mmol) in 2.5 mL of dichloromethane was added 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (EDCI) (0.057 g, 0.298 mmol). The reaction was stirred at room temperature for 10 min before 3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)]-1H-indazol-3-yl}phenylamine (0.150 g, 0.248 mmol) dissolved in 1 mL of dichloromethane, was added to the solution. The reaction was stirred at room temperature for 3 hours. The reaction mixture was then partitioned between water and dichloromethane. The crude material that was obtained from evaporation of the extracts was not purified further. (Yield not calculated) ES-MS (m/z) 751 [M+H]+.
	In dichloromethane	299.A A. A. N-(3-{1-Perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)](1H-indazol-3-yl)}phenyl)-2-phenoxypropanamide To a solution of 2-phenoxypropanoic acid (0.045 g, 0.274 mmol) in 2.5 mL of dichloromethane was added 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (EDCI) (0.057 g, 0.298 mmol). The reaction was stirred at room temperature for 10 min before 3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)]-1H-indazol-3-yl}phenylamine (0.150 g, 0.248 mmol) dissolved in 1 mL of dichloromethane, was added to the solution. The reaction was stirred at room temperature for 3 hours. The reaction mixture was then partitioned between water and dichloromethane. The crude material that was obtained from evaporation of the extracts was not purified further. (Yield not calculated) ES-MS (m/z) 751 [M+H]+.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2002/103229, 2002, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2004/127536, 2004, A1
[3]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2005/9876, 2005, A1

38
[ 940-31-8 ]
[ 42412-84-0 ]

Yield	Reaction Conditions	Operation in experiment
94.3%	With sulfuric acid	5 Ethyl phenoxypropionate EXAMPLE 5 Ethyl phenoxypropionate Phenoxypropionic acid (6.64 g, 0.04 mol) is mixed with excess ethanol (10 ml) and concentrated sulfuric acid (0.5 ml) is added. The reaction mixture is refluxed for 3 hours, cooled to room temperature and concentrated. The residue is washed with 1N NaOH and brine, dried (Na2 SO4), and concentrated to yield 7.32 g (94.3% yield) of the ester which can be used directly for the subsequent reaction without further purification. 1 H nmr (CDCl3) δ: 7.22-7.29 (overlap 2H, phenyl H), 6.88-6.966 (overlap 3H, phenyl H), 4.10-4.20 (overlap 4H, 2CH2 O), 2.73 (t, 2H. J=6.4 Hz, CH2), 1.23 (t, 3H, J=7.1 Hz, CH3); 13 C nmr (CDCl3) δ: 170.7, 158.7, 129.4(2C), 120.9 114.6(2C), 63.4, 60.5, 34.5, 14.1.

Reference： [1]Current Patent Assignee: APOTEX INC - US5900485, 1999, A

39
4-Bromo-1-(bromomethyl)-2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile [ No CAS ]
[ 940-31-8 ]
[3-Bromo-5-(;-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methyl 2-phenoxypropionate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In N,N-dimethyl-formamide	1 Preparation of [3-Bromo-5-(;-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methyl 2-phenoxypropionate STR18 EXAMPLE 1 Preparation of [3-Bromo-5-(;-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methyl 2-phenoxypropionate STR18 4-Bromo1-(bromomethyl)-2-(p-chlorophenyl)-5-(trifluormethyl)pyrrole-3-carbonitrile (2.5 g, 5.7 mmol) is added to a mixture of 2-phenoxypropionic acid (1.9 g, 11.4 mmol) and sodium hydroxide (0.46 g, 11.4 mmol) in N,N-dimethylformamide. The reaction mixture is stirred for one hour at 50° C. and diluted with a 3:2 ethyl acetate/water mixture. The organic phase is separated, dried over MgSO4 and concentrated in vacuo to obtain a tan oil. The oil is crystallized from 2-propanol to give the title product as a yellow solid (2.7 g, mp 101°-103° C.).

Reference： [1]Current Patent Assignee: ZOETIS INC. - US5286741, 1994, A

40
[ 908094-01-9 ]
[ 940-31-8 ]
[ 74-88-4 ]
[ 72278-52-5 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; diisopropylamine In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; water	R.91 Methyl 2-methyl-2-phenoxypropionate 91 STR110 REFERENCE EXAMPLE 91 Methyl 2-methyl-2-phenoxypropionate 91 STR110 To a solution of diisopropylamine (37.00 ml, 0.264 mol) in anhydrous THF (200 ml) was added dropwise under argon atmosphere n-butyl lithium in hexane (1.62N, 163 ml, 0.264 mol) at 0° C. The reaction mixture was stirred for 30 min. at 0° C. To this was added dropwise a solution of 2-phenoxypropionic acid (20.00 g, 0.120 mol) in anhydrous THF (60 ml) and the mixture was stirred for 10 min. at 0° C. To the mixture was added dropwise HMPA (45.9 ml, 0.264 mol) and the resulting mixture was stirred for 20 min. To the mixture was added dropwise methyl iodide (15.7 ml, 0.252 mol) at 0° C. The mixture was then stirred for 4 hrs. at room temperature. The resulting mixture was acidified with 6N hydrochloric acid to pH 2 and extracted with ethyl acetate (50 ml*4). The ethyl acetate layers were washed with 50 ml of water and with 50 ml of brine, dried over anhydrous sodium sulfate, and concentrated. To the residue in 100 ml of ether was added dropwise a solution of diazomethane in ether (270 ml) at 0° C. Concentration and distillation of the solution thus obtained gave methyl 2-methyl-2-phenoxypropionate (22.8052 g, yield: 96.7%, b.p. 64.5°-75.3° C./0.22 mmHg) as a colourless oil. The product was assigned the structure by the following data. IR(liquid film): 3000, 2950, 2900, 2820, 1735, 1595, 1490, 1460, 1385, 1365, 1288, 1233, 1193, 1175, 1140, 1066, 1023, 983, 885, 822, 750, 695 cm-1. NMR(100 MHz, CDCl3, δ): 1.59(6H, s); 3.77(3H, s); 6.70-7.40(5H, m).

Reference： [1]Current Patent Assignee: TORAY INDUSTRIES INC - US4775692, 1988, A

41
phosphorous oxychloride (POCl₃) [ No CAS ]
[ 940-31-8 ]
5-(1-phenoxyethyl)-2-amino-1,3,4-thiadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; trichlorophosphate In 1,4-dioxane; water	I.a a. a. formation of 5-(1-phenoxyethyl)-2-amino-1,3,4-thiadiazole A 1,000 milliliter, 3-neck flask equipped with a Claisen adaptor, paddle stirrer, thermometer, addition funnel and condenser, was charged with 100 grams (0.602 moles) of 2-phenoxypropanoic acid, (54.8 grams, 0.602 mole) of thiosemicarbazide and 300 ml. of dioxane. The slurry was heated to 85° C. and the addition funnel was charged with phosphorous oxychloride (POCl3). The POCl3 was slowly added (for 70 minutes) while maintaining the temperature within 90°-95° C., and then stirred for an additional 20 minutes. It was refluxed for 105 minutes and cooled. The flask was evacuated by using a water aspirator to remove volatiles (HCl, POCl3 and some dioxane), leaving a viscous residue to which 400 ml of water was added and the residue emulsified. A 50 percent solution of NaOH was added until the pH of the solution was 10, and a solid precipitate formed. The solid precipitate was filtered off, washed with water, air dried, then dried in a vacuum oven at 60° C. to a granular grey solid which was recrystallized from H2 O/ethanol mixture, filtered and then dried in a vacuum oven at 60° C. to white needles of 5-(1-phenoxyethyl)-2-amino- 1,3,4-thiadiazole. (Melting point 157°-167° C.).

Reference： [1]Current Patent Assignee: PFIZER INC - US4233057, 1980, A

42
[ 98-03-3 ]
[ 940-31-8 ]
[ 401791-32-0 ]

Yield	Reaction Conditions	Operation in experiment
	With diisopropylamine In tetrahydrofuran; hexane; n-heptane; ethyl acetate	90.A 3-Hydroxy-2-methyl-2-phenoxy-3-thiophen-2-yl-propionic Acid Step A 3-Hydroxy-2-methyl-2-phenoxy-3-thiophen-2-yl-propionic Acid To a 2.0 M solution of LDA in THF/heptane/ethyl benzene (200 mL, 408 mmol) cooled by an ice/acetone bath, a 0.75 M solution of 2-phenoxypropionic acid (30.8 g, 185 nmol) in THF (250 mL) was added dropwise over 30 min, keeping the reaction temperature below -10° C. After allowing the reaction mixture to stir for 15 min, a 0.75 M solution of 2-thiophenecarboxaldehyde (20.8 g, 185 mmol) in THF (250 mL) was added dropwise over the course of 1 h, maintaining the reaction temperature below -5° C. After stirring for 5 min at 0° C., HPLC analysis showed the reaction to be complete. The reaction was poured into ice water (600 mL) and ether (500 mL) was added. Hexane (1.0 L) was added and the layers were separated. The aqueous layer was further extracted with Et2O: hexane (1:2) (750 mL). The organic layers were checked for product then discarded. Ethyl acetate (500 mL) was added to the aqueous layer, acidified to pH=2 with conc. HCl (18 mL), and the layers were separated. The aqueous layer was extracted with ethyl acetate (2*200 mL). The organic layer was dried over NaCl and solvent removed in vacuo to provide 50.0 g of crude product. The product was used in the next step without further purification: 1H NMR (400 MHz, CDCl3) δ 7.33 (dd, 1H), 7.26 (m, 2H), 7.12 (m, 1H), 7.04 (d, 1H), 6.97 (m, 2H), 6.87 (dd, 1H), 5.37 (s, 1H), 1.40 (s, 3H); MS (EI-) 277.1 (M-1)-.

Reference： [1]Current Patent Assignee: ELI LILLY & CO - US2004/97590, 2004, A1

43
[ 2426-87-1 ]
[ 940-31-8 ]
[ 401468-69-7 ]

Yield	Reaction Conditions	Operation in experiment
	With diisopropylamine In tetrahydrofuran; diethyl ether; hexane; cyclohexane	11.A 3-(4-Benzyloxy-3-methoxyphenyl)-3-hydroxy-2-methyl-2-phenoxypropionic Acid Step A 3-(4-Benzyloxy-3-methoxyphenyl)-3-hydroxy-2-methyl-2-phenoxypropionic Acid A stirred solution of LDA in cyclohexane (1.5 M) was cooled to -20° C., to which a solution of 2-phenoxypropionic acid (10 g, 60.2 mmol) in THF (80.3 mL) was slowly added, keeping the temperature below -10° C. The resulting dianion solution was stirred for 15 min, then a solution of 4-benzyloxy-3-methoxybenzaldehyde (14.58 g, 60.2 mmol) in THF (80.3 mL) was added over 1 h, maintaining temperature below -10° C. Fifteen minutes after completion of aldehyde addition, the reaction mixture was poured onto ice water (200 mL), and extracted using 1:2 Et2O:hexane (500 mL). The aqueous layer was isolated, extracted again with 1:2 Et2O:hexane (240 mL), then acidified with concentrated HCl until pH=3. The product acid was extracted into EtOAc (2*165 mL), which was dried over Na2SO4 and concentrated to an orange paste (16.5 g crude, 67%): MS (EI) 426.2 (M+NH4)+, 407.2 (M-H)-.
	With diisopropylamine In tetrahydrofuran; diethyl ether; hexane; cyclohexane	7.A A. A. 3-(4-Benzyloxy-3-methoxyphenyl)-3-hydroxy-2-methyl-2-phenoxypropionic acid A stirred solution of LDA in cyclohexane (1.5 M) was cooled to -20° C., to which a solution of 2-phenoxypropionic acid (10 g, 60.2 mmol) in TBF (80.3 mL) was slowly added, keeping the temperature below -10° C. The resulting dianion solution was stirred for 15 min, then a solution of 4-benzyloxy-3-methoxybenzaldehyde (14.58 g, 60.2 mmol) in THF (80.3 mL) was added over 1 h, maintaining temperature below -10° C. Fifteen minutes after completion of aldehyde addition, the reaction mixture was poured onto ice water (200 mL), and extracted using 1:2 Et2O:hexane (500 mL). The aqueous layer was isolated, extracted again with 1:2 Et2O:hexane (240 mL), then acidified with concentrated HCl until pH=3. The product acid was extracted into ethyl acetate (2*165 mL), which was dried over Na2SO4 and concentrated to an orange paste (16.5 g crude, 67%): MS (EI) 426.2 (M+NH4)+, 407.2 (M-H)-.

Reference： [1]Current Patent Assignee: ELI LILLY & CO - US2004/97590, 2004, A1
[2]Current Patent Assignee: LIGAND PHARMACEUTICALS INC; ELI LILLY & CO - US2004/138277, 2004, A1

44
[ 940-31-8 ]
[ 105118-15-8 ]
[ 94050-90-5 ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 5950 - 5953

45
[ 3307-39-9 ]
[ 940-31-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-(4-chlorophenoxy)propionic acid With 1,2-diphenyl-1,2-disodiumethane In tetrahydrofuran at 0 - 20℃; for 12h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water chemoselective reaction;	4.3. Reductive cleavage of chloronated aryloxyalkanoic acids 1a-f. General procedure General procedure: To 10 mL of a 0.2 M solution of a SET reagent 2 or 3 (2 mmol), cooled to 0 °C, was added a solution of the appropriate aryloxyalkanoic acid 1 (for the relative molar ratios, see Table 1), dissolved in dry THF (5 mL). Reactions with Li or Na metal were run under closely related reaction conditions, by adding solutions of the appropriate aryloxyalkanoic acid 1 to suspension of the freshly cut metal in dry THF.Each mixture was vigorously stirred and allowed to reach rt for 12 h, after which time it was quenched by slow dropwise addition of H2O (15 mL). The organic solvent was evaporated in vacuo and the resulting mixture was extracted with CH2Cl2 (3×10 mL). The aqueous phase was acidified with 1 N HCl, extracted with CH2Cl2 (3×10 mL), and the organic phases were collected, washed with H2O (1×10 mL), brine (10 mL) and dried (Na2SO4). After evaporation of the solvent, the resulting mixture was analyzed by 1H NMR spectroscopy.

Reference： [1]Location in patent: experimental part Azzena, Ugo; Pittalis, Mario [Tetrahedron, 2011, vol. 67, # 19, p. 3360 - 3362]

46
[ 940-31-8 ]
[ 62784-66-1 ]
[ 1213744-22-9 ]
[ 1345458-52-7 ]
[ 1129-46-0 ]
[ 1912-23-8 ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 11296 - 11304
[2]Heterocycles,2012,vol. 86,p. 1227 - 1252

47
[ 940-31-8 ]
[ 59301-23-4 ]
[ 1391916-82-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere;

Reference： [1]Carlsson, Jens; Tosh, Dilip K.; Phan, Khai; Gao, Zhan-Guo; Jacobson, Kenneth A. [ACS Medicinal Chemistry Letters, 2012, vol. 3, # 9, p. 715 - 720]

48
[ 940-31-8 ]
3-(3-tolyl)-1H-1,2,4-triazol-5-amine [ No CAS ]
[ 1391916-83-8 ]

Yield	Reaction Conditions	Operation in experiment
81%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere;

Reference： [1]Carlsson, Jens; Tosh, Dilip K.; Phan, Khai; Gao, Zhan-Guo; Jacobson, Kenneth A. [ACS Medicinal Chemistry Letters, 2012, vol. 3, # 9, p. 715 - 720]

49
[ 940-31-8 ]
[ 349609-85-4 ]
[ 1245750-90-6 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 4028 - 4043

50
[ 940-31-8 ]
C₂₁H₂₂N₄O [ No CAS ]
C₃₀H₃₀N₄O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	20 Synthesis of final compound 20 Synthesis of final compound 20: A mixture of J-l (100 mg, 0.289 mmol), 2-phenoxypropionic acid (62.4 mg, 0.375 mmol), EDCI (83 mg, 0.433 mmol), HOBT (58.5 mg, 0.433 mmol) and NEt3 (61 μ, 0.433 mmol) in CH2C12 (5 mL) was stirred at RT overnight. Water was added and the layers were decanted. The organic layer was washed with water, dried over MgS04, filtered and the solvent was evaporated. The crude compound was purified by chromatography over silica gel (15-40 μιη, 30 g) with CH2Cl2/MeOH/NH4OH 97.5/2.5/0.1. The solvent was evaporated to give final compound 20 (64%).
64%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃;	Synthesis of Final Compound 20: A mixture of J-1 (100 mg, 0.289 mmol), 2-phenoxypropionic acid (62.4 mg, 0.375 mmol), EDCI (83 mg, 0.433 mmol), HOBT (58.5 mg, 0.433 mmol) and NEt3 (61 μL, 0.433 mmol) in CH2Cl2 (5 mL) was stirred at RT overnight. Water was added and the layers were decanted. The organic layer was washed with water, dried over MgSO4, filtered and the solvent was evaporated. The crude compound was purified by chromatography over silica gel (15-40 μm, 30 g) with CH2Cl2/MeOH/NH4OH 97.5/2.5/0.1. The solvent was evaporated to give final compound 20 (64%).
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃;	Synthesis of Final Compound 20: A mixture of J-1 (100 mg, 0.289 mmol), 2-phenoxypropionic acid (62.4 mg, 0.375 mmol), EDCI (83 mg, 0.433 mmol), HOBT (58.5 mg, 0.433 mmol) and NEt3 (61 μL, 0.433 mmol) in CH2Cl2 (5 mL) was stirred at RT overnight. Water was added and the layers were decanted. The organic layer was washed with water, dried over MgSO4, filtered and the solvent was evaporated. The crude compound was purified by chromatography over silica gel (15-40 μm, 30 g) with CH2Cl2/MeOH/NH4OH 97.5/2.5/0.1. The solvent was evaporated to give final compound 20 (64%).

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2013/164337, 2013, A1 Location in patent: Page/Page column 37-38
[2]Current Patent Assignee: JOHNSON & JOHNSON INC - US2015/87651, 2015, A1 Location in patent: Paragraph 0139-0140
[3]Current Patent Assignee: JOHNSON & JOHNSON INC - US2017/334880, 2017, A1 Location in patent: Paragraph 0137-0138

51
[ 940-31-8 ]
[ 954279-15-3 ]
[ 1616074-85-1 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 24℃; for 16h;	19.3 Step 3: N-(3-(3,4-dihydroisoquinolin-2(lH)-yl)-2-hydroxypropyl)-2- phenoxypropanamide To a solution of 2-phenoxypropanoic acid (200 mg, 1.2 mmol ) in DMF (4 ml) was added TEA 364 mg, 3.6 mmol), HOBt (243 mg, 1.8 mmol), EDCI (346 mg, 1.8 mmol) and 1- amino-3-(3,4-dihydroisoquinolin-2(lH)-yl)propan-2-ol (297 mg, 1.44 mmol) at 24°C. The reaction mixture was stirred for 16 h until TLC showed completion of the reaction. After evaporation of the solvent, the residue was purified by prep-HPLC separation to give the title compound as the formate salt (34 mg, 8%). 1H NMR (500 MHz, MeOD): δ 8.40 (s, 1H), 7.34-7.25 (m, 5H), 7.17 (d, J = 7.2 Hz, 1H), 7.00-6.96 (m, 3H), 4.78-4.76 (m, 1H), 4.26-4.11 (m, 3H), 3.43-3.33 (m, 4H), 3.14-3.12 (m, 2H), 3.08-3.02 (m, 1H), 2.95-2.90 (m, 1H), 1.57 (d, J = 6.4 Hz, 3H)ppm; ESI-MS (m/z): 354.2 [M+l] +.

Reference： [1]Current Patent Assignee: EPIZYME, INC. - WO2014/100730, 2014, A1 Location in patent: Paragraph 00276

52
[ 940-31-8 ]
[ 118-92-3 ]
DL-N-(2-phenoxypropionyl)anthranilic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	Stage #1: 2-phenoxypropionic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 6h; Stage #2: anthranilic acid In N,N-dimethyl-formamide at 20℃; for 12h;	DL-N-(2-Phenoxypropionyl)anthranilic acid (5) To a solution of DL-2-phenoxypropionic acid (1 g,6.20 mmol) in N,N-dimethylformamide (10 mL) was added EDCI (1.4 g, 7.40 mmol) and reacted at room temperaturefor 6 h. This reaction mixture was added anthranilic acid (420 mg, 3 mmol) and stirred at room temperature for 12 h. The reaction mixture was added with water and extracted with dichloromethane and the organic extracts were dried with anhydrous MgSO4, filtered and concentrated to give crude brown solid. The crude compound was purified by column chromatography (ethyl acetate:n-hexane = 1:3) to yield as a pale yellow powder.Yield: 865 mg (56 %); m.p.: 133-134 °C; 1H NMR(400 MHz, CDCl3) δ: 1.71 (3H, t, J = 6.4 Hz, OCHCH3),4.86 (1H, q, J = 6.4 Hz, OCHCH3), 7.05 (3H, m, H-20,40,60), 7.30 (2H, t, J = 6.8 Hz, H-30,50), 7.17 (1H, t,J = 6.8 Hz, H-5), 7.64 (1H, t, J = 8.4 Hz, H-4), 8.14 (1H,d, J = 8.0 Hz, H-6), 8.85 (1H, d, J = 8.4 Hz, H-3), 11.81(1H, s, NHCO); 13C NMR (100 MHz, CDCl3) δ: 18.9(OCHCH3), 75.0 (OCHCH3), 114.6 (C-1), 115.3 (C-20,60),120.5 (C-3), 121.9 (C-40), 123.2 (C-5), 129.7 (C-30,50),131.8 (C-6), 135.7 (C-4), 141.3 (C-2), 156.9 (C-10), 171.7(COO), 171.9 (NHCO); GC-MS (EI) m/z: 267 [M-1-OH]+.

Reference： [1]Kim, Sohee; Shin, Beom Soo; Ma, Eunsook [Archives of Pharmacal Research, 2015, vol. 38, # 6, p. 1147 - 1156]

53
[ 940-31-8 ]
[ 20265-29-6 ]
[PhO(Me)CHCO₂]₂Sb(C₆H₅)₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: 2-phenoxypropionic acid With potassium hydroxide In methanol for 0.5h; Schlenk technique; Reflux; Stage #2: triphenylantimony dichloride In methanol for 8h; Schlenk technique; Reflux;	2.2.1. [PhO(Me)CHCO2]2Sb(C6H5)3 (1). The reaction was carried out under air with theuse of standard Schlenk technique. 2-Phenoxypropionic acid (0.665 g, 4 mmol) and potassiumhydroxide (0.224 g, 4 mmol) were added to methanol (80 mL) and heated under refluxwith stirring for 0.5 h. After the addition of triphenylantimony dichloride (0.848 g, 2 mmol)to the reactor, the reaction mixture was refluxed for 8 h more. The reaction solution thusobtained was filtered and evaporated under vacuum to form a white solid, and then recrystallizedfrom dichloromethane-petroleum ether (v/v 3 : 1) to give colorless single crystals of1. Yield: 74%, m.p.: 156-159 °C. Anal. Calcd for: C36H33O6Sb: C, 63.27; H, 4.87%.Found: C, 63.31; H, 4.90%. IR (KBr, cm-1): 1664 ν(C=O), 1375 ν(C-O), 433 ν(Sb-C),461 ν(Sb-O). 1H NMR (400 MHz, CDCl3, ppm): 7.80-6.58 [m, 25H, Ph-Sb, Ph(O-CH)];4.46 (q, 2H, J = 6.8 Hz, -CH-); 1.32 (d, 6H, J = 6.8 Hz, CH3-); 13C NMR (100 MHz,CDCl3, ppm): 175.55 (COO); 158.14; 136.72, 134.23, 131.41, 129.46, 129.42, 120.93,115.03 (aryl group); 73.22 (-CH-); 18.56 (CH3-).

Reference： [1]Geng, Honglin; Hong, Min; Yang, Yuanguang; Li, Dacheng; Li, Xuetong; Liu, Fulin; Niu, Meiju [Journal of Coordination Chemistry, 2015, vol. 68, # 16, p. 2938 - 2952]

54
[ 110519-06-7 ]
[ 940-31-8 ]
[PhO(Me)CHCO₂]₂Sb(4-FC₆H₄)₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	Stage #1: 2-phenoxypropionic acid With potassium hydroxide In methanol for 0.5h; Schlenk technique; Reflux; Stage #2: tris(p-fluorophenyl)antimony dichloride In methanol for 8h; Schlenk technique; Reflux;	2.2.1. [PhO(Me)CHCO2]2Sb(C6H5)3 (1). General procedure: The reaction was carried out under air with theuse of standard Schlenk technique. 2-Phenoxypropionic acid (0.665 g, 4 mmol) and potassiumhydroxide (0.224 g, 4 mmol) were added to methanol (80 mL) and heated under refluxwith stirring for 0.5 h. After the addition of triphenylantimony dichloride (0.848 g, 2 mmol)to the reactor, the reaction mixture was refluxed for 8 h more. The reaction solution thusobtained was filtered and evaporated under vacuum to form a white solid, and then recrystallizedfrom dichloromethane-petroleum ether (v/v 3 : 1) to give colorless single crystals of1.

Reference： [1]Geng, Honglin; Hong, Min; Yang, Yuanguang; Li, Dacheng; Li, Xuetong; Liu, Fulin; Niu, Meiju [Journal of Coordination Chemistry, 2015, vol. 68, # 16, p. 2938 - 2952]

55
[ 159226-57-0 ]
[ 940-31-8 ]
[PhO(Me)CHCO₂]₂Sb(3-FC₆H₄)₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: 2-phenoxypropionic acid With potassium hydroxide In methanol for 0.5h; Schlenk technique; Reflux; Stage #2: tris(m-fluorophenyl)antimony(V) dichloride In methanol for 8h; Schlenk technique; Reflux;	2.2.1. [PhO(Me)CHCO2]2Sb(C6H5)3 (1). General procedure: The reaction was carried out under air with theuse of standard Schlenk technique. 2-Phenoxypropionic acid (0.665 g, 4 mmol) and potassiumhydroxide (0.224 g, 4 mmol) were added to methanol (80 mL) and heated under refluxwith stirring for 0.5 h. After the addition of triphenylantimony dichloride (0.848 g, 2 mmol)to the reactor, the reaction mixture was refluxed for 8 h more. The reaction solution thusobtained was filtered and evaporated under vacuum to form a white solid, and then recrystallizedfrom dichloromethane-petroleum ether (v/v 3 : 1) to give colorless single crystals of1.

Reference： [1]Geng, Honglin; Hong, Min; Yang, Yuanguang; Li, Dacheng; Li, Xuetong; Liu, Fulin; Niu, Meiju [Journal of Coordination Chemistry, 2015, vol. 68, # 16, p. 2938 - 2952]

56
[ 940-31-8 ]
[ 1441421-67-5 ]
[PhO(Me)CHCO₂]₂Sb(3,4,5-F₃C₆H₂)₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: 2-phenoxypropionic acid With potassium hydroxide In methanol for 0.5h; Schlenk technique; Reflux; Stage #2: tri(3,4,5-trifluorophenyl)antimony dichloride In methanol for 8h; Schlenk technique; Reflux;	2.2.1. [PhO(Me)CHCO2]2Sb(C6H5)3 (1). General procedure: The reaction was carried out under air with theuse of standard Schlenk technique. 2-Phenoxypropionic acid (0.665 g, 4 mmol) and potassiumhydroxide (0.224 g, 4 mmol) were added to methanol (80 mL) and heated under refluxwith stirring for 0.5 h. After the addition of triphenylantimony dichloride (0.848 g, 2 mmol)to the reactor, the reaction mixture was refluxed for 8 h more. The reaction solution thusobtained was filtered and evaporated under vacuum to form a white solid, and then recrystallizedfrom dichloromethane-petroleum ether (v/v 3 : 1) to give colorless single crystals of1.

Reference： [1]Geng, Honglin; Hong, Min; Yang, Yuanguang; Li, Dacheng; Li, Xuetong; Liu, Fulin; Niu, Meiju [Journal of Coordination Chemistry, 2015, vol. 68, # 16, p. 2938 - 2952]

57
[ 524-38-9 ]
[ 940-31-8 ]
2,7-dioxoisoindol-1-yl (RS)-2-phenoxypropanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;
76%	With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 15h;
65%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 24h;

With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere;

Reference： [1]Li, Jiacheng; Siang Tan, Suan; Kyne, Sara Helen; Wai Hong Chan, Philip [Advanced Synthesis and Catalysis, 2022, vol. 364, # 4, p. 802 - 810]
[2]Schwarz, Johanna; König, Burkhard [Green Chemistry, 2016, vol. 18, # 17, p. 4743 - 4749]
[3]Bartashevich, Ekaterina V.; Chulakov, Evgeny N.; Ezhikova, Marina A.; Gruzdev, Dmitry A.; Kodess, Mikhail I.; Korolyova, Marina A.; Krasnov, Victor P.; Levit, Galina L.; Tumashov, Andrey A.; Vakarov, Sergey A. [Organic and Biomolecular Chemistry, 2022, vol. 20, # 4, p. 862 - 869]
[4]Jin, Songyang; Geng, Xinxin; Li, Yujun; Zheng, Ke [European Journal of Organic Chemistry, 2021, vol. 2021, # 6, p. 969 - 972]

58
[ 1462-12-0 ]
[ 940-31-8 ]
diethyl 2-(3-phenoxybutan-2-yl)malonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium carbonate; 9-(2-mesityl)-10-methylacridinium perchlorate In water; acetonitrile at 20℃; for 44h; Microwave irradiation; diastereoselective reaction;

Reference： [1]Ramirez, Nieves P.; Gonzalez-Gomez, Jose C. [European Journal of Organic Chemistry, 2017, vol. 2017, # 15, p. 2154 - 2163]

59
[ 940-31-8 ]
(S)-4-(3-minopiperidin-1-yl)coumarin [ No CAS ]
C₂₃H₂₄N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.5h;	(R)- and (S)-2-Phenoxypropanoic acid + 6-CDA (entry 8) General procedure: Method A: CDA (1, 4, or 7) and carboxylic acid dissolved in DCM were stirred for 15 min at roomtemperature. N,N′-Dicyclohexylcarbodiimide (DCC) was then added, and the mixture was stirred for 30min at room temperature

Reference： [1]Wada, Koji; Goto, Mizuko; Yamashita, Hiroshi; Nagasawa, Kazuo [Heterocycles, 2017, vol. 94, # 5, p. 964 - 978]

60
[ 940-31-8 ]
(S)-4-(3-aminoazepan-1-yl)coumarin [ No CAS ]
C₂₄H₂₆N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.5h;	(R)- and (S)-2-Phenoxypropanoic acid + 7-CDA (entry 8) General procedure: Method B: CDA, carboxylic acid, and DMAP dissolved in DCM were stirred for 15 min at roomtemperature. DCC was added, and the mixture was stirred for 30 min at room temperature

Reference： [1]Wada, Koji; Goto, Mizuko; Yamashita, Hiroshi; Nagasawa, Kazuo [Heterocycles, 2017, vol. 94, # 5, p. 964 - 978]

61
[ 940-31-8 ]
(S)-4-(3-aminopyrrolidin-1-yl)coumarin [ No CAS ]
C₂₂H₂₂N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.5h;	(R)- and (S)-2-Phenoxypropanoic acid + 5-CDA (entry 8) General procedure: Method A: CDA (1, 4, or 7) and carboxylic acid dissolved in DCM were stirred for 15 min at roomtemperature. N,N′-Dicyclohexylcarbodiimide (DCC) was then added, and the mixture was stirred for 30min at room temperature

Reference： [1]Wada, Koji; Goto, Mizuko; Yamashita, Hiroshi; Nagasawa, Kazuo [Heterocycles, 2017, vol. 94, # 5, p. 964 - 978]

62
[ 940-31-8 ]
[ 75927-49-0 ]
4,4,5,5-tetramethyl-2-(3-phenoxybutyl)-1,3,2-dioxaborolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; caesium carbonate In N,N-dimethyl acetamide at 35℃; for 40h; Sealed tube; Inert atmosphere; Irradiation;

Reference： [1]Noble, Adam; Mega, Riccardo S.; Pflästerer, Daniel; Myers, Eddie L.; Aggarwal, Varinder K. [Angewandte Chemie - International Edition, 2018, vol. 57, # 8, p. 2155 - 2159][Angew. Chem., 2018, vol. 130, p. 2177 - 2181,5]

63
[ 940-31-8 ]
[ 22821-76-7 ]
[ 6437-44-1 ]

Reference： [1]Organic Letters,2019

64
[ 64-18-6 ]
[ 940-31-8 ]
[ 954279-15-3 ]
[ 1616077-45-2 ]

Yield	Reaction Conditions	Operation in experiment
8%	Stage #1: 2-phenoxypropionic acid; 1-amino-3-(3,4-dihydroisoquinoline-2(1H)-yl)propan-2-ol With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 24℃; for 16h; Stage #2: formic acid	19.3 Step 3: N-(3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)-2-phenoxypropanamide To a solution of 103 2-phenoxypropanoic acid (200 mg, 1.2 mmol) in 47 DMF (4 ml) was added 32 TEA 364 mg, 3.6 mmol), 105 HOBt (243 mg, 1.8 mmol), EDCI (346 mg, 1.8 mmol) and 6 1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol (297 mg, 1.44 mmol) at 24° C. The reaction mixture was stirred for 16 h until TLC showed completion of the reaction. After evaporation of the solvent, the residue was purified by prep-HPLC separation to give the 96 title compound as the formate salt (34 mg, 8%). 1H NMR (500 MHz, MeOD): δ 8.40 (s, 1H), 7.34-7.25 (m, 5H), 7.17 (d, J=7.2 Hz, 1H), 7.00-6.96 (m, 3H), 4.78-4.76 (m, 1H), 4.26-4.11 (m, 3H), 3.43-3.33 (m, 4H), 3.14-3.12 (m, 2H), 3.08-3.02 (m, 1H), 2.95-2.90 (m, 1H), 1.57 (d, J=6.4 Hz, 3H) ppm; ESI-MS (m/z): 354.2 [M+1]+.

Reference： [1]Current Patent Assignee: EPIZYME, INC. - US2019/83482, 2019, A1 Location in patent: Paragraph 0259-0270

65
[ 940-31-8 ]
[ 89295-32-9 ]
ethyl 2-methylene-4-phenoxypentanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With riboflavin tetraacetate In acetonitrile at 25℃; Inert atmosphere; Irradiation; Sealed tube;

Reference： [1]Ramirez, Nieves P.; Lana-Villarreal, Teresa; Gonzalez-Gomez, Jose C. [European Journal of Organic Chemistry, 2020, vol. 2020, # 10, p. 1539 - 1550]

66
[ 940-31-8 ]
benzyl 2-((phenylsulfonyl)methyl)acrylate [ No CAS ]
benzyl 2-methylene-4-phenoxypentanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With riboflavin tetraacetate In acetonitrile at 25℃; Inert atmosphere; Irradiation; Sealed tube;

Reference： [1]Ramirez, Nieves P.; Lana-Villarreal, Teresa; Gonzalez-Gomez, Jose C. [European Journal of Organic Chemistry, 2020, vol. 2020, # 10, p. 1539 - 1550]

67
[ 940-31-8 ]
allyl 2-((phenylsulfonyl)methyl)acrylate [ No CAS ]
allyl 2-methylene-4-phenoxypentanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With riboflavin tetraacetate In acetonitrile at 25℃; Inert atmosphere; Irradiation; Sealed tube;

Reference： [1]Ramirez, Nieves P.; Lana-Villarreal, Teresa; Gonzalez-Gomez, Jose C. [European Journal of Organic Chemistry, 2020, vol. 2020, # 10, p. 1539 - 1550]

68
[ 940-31-8 ]
[ 3480-90-8 ]
((4-chloropent-4-en-2-yl)oxy)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With riboflavin tetraacetate In acetonitrile at 25℃; Inert atmosphere; Irradiation; Sealed tube;

Reference： [1]Ramirez, Nieves P.; Lana-Villarreal, Teresa; Gonzalez-Gomez, Jose C. [European Journal of Organic Chemistry, 2020, vol. 2020, # 10, p. 1539 - 1550]

69
[ 940-31-8 ]
[ 2525-55-5 ]
((4-phenoxypent-1-en-2-yl)sulfonyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With riboflavin tetraacetate In acetonitrile at 25℃; Inert atmosphere; Irradiation; Sealed tube;

Reference： [1]Ramirez, Nieves P.; Lana-Villarreal, Teresa; Gonzalez-Gomez, Jose C. [European Journal of Organic Chemistry, 2020, vol. 2020, # 10, p. 1539 - 1550]

70
[ 940-31-8 ]
[ 74866-37-8 ]
(4-phenoxypent-1-en-2-yl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With riboflavin tetraacetate In acetonitrile at 25℃; Inert atmosphere; Irradiation; Sealed tube;

Reference： [1]Ramirez, Nieves P.; Lana-Villarreal, Teresa; Gonzalez-Gomez, Jose C. [European Journal of Organic Chemistry, 2020, vol. 2020, # 10, p. 1539 - 1550]

71
[ 940-31-8 ]
5-phenyl-2-((phenylsulfonyl)methyl)pent-2-enenitrile [ No CAS ]
2-methylene-3-phenethyl-4-phenoxypentanenitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With riboflavin tetraacetate In acetonitrile at 25℃; Inert atmosphere; Irradiation; Sealed tube;

Reference： [1]Ramirez, Nieves P.; Lana-Villarreal, Teresa; Gonzalez-Gomez, Jose C. [European Journal of Organic Chemistry, 2020, vol. 2020, # 10, p. 1539 - 1550]

72
[ 940-31-8 ]
[ 64345-00-2 ]
2-(1-phenoxyethyl)benzo[d]thiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With riboflavin tetraacetate In acetonitrile at 25℃; Sealed tube; Inert atmosphere; Irradiation;

Reference： [1]Ramirez, Nieves P.; Lana-Villarreal, Teresa; Gonzalez-Gomez, Jose C. [European Journal of Organic Chemistry, 2020, vol. 2020, # 10, p. 1539 - 1550]

73
[ 940-31-8 ]
[ 87120-72-7 ]
tert-butyl 4-(2-phenoxypropanamido)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 18h;	2-phenoxy-N-(piperidin-4-yl)propanamide hydrochloride Step 1: Synthesis of tert-butyl 4-(2-phenoxypropanamido)piperidine-1-carboxylate A mixture of tert-butyl 4-aminopiperidine-1-carboxylate (500 mg, 2.497 mmol), 2-phenoxypropanoic acid (415 mg, 2.497 mmol), HATU (1139 mg, 3.000 mmol) and N,N-diisopropylethylamine (0.65 mL, 3.74 mmol) in dry N,N-Dimethylformamide (15 mL) was stirred at room temperature for 18 h. The reaction mixture was poured out into water (200 mL). The resulting mixture was extracted with diethyl ether. Combined organic extracts were washed with saturated aqueous sodium bicarbonate, dried with sodium sulfate and concentrated in vacuo. The crude product was used as such.

Reference： [1]Leenders, Ruben; van de Sande, Marc; Bonfanti, Jean-François [Tetrahedron Letters, 2020, vol. 61, # 1]

74
[ 100-02-7 ]
[ 940-31-8 ]
4-nitrophenyl (RS)-2-phenoxypropanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 24h;
	With dicyclohexyl-carbodiimide In dichloromethane at 20℃; Schlenk technique; Inert atmosphere;

Reference： [1]Bartashevich, Ekaterina V.; Chulakov, Evgeny N.; Ezhikova, Marina A.; Gruzdev, Dmitry A.; Kodess, Mikhail I.; Korolyova, Marina A.; Krasnov, Victor P.; Levit, Galina L.; Tumashov, Andrey A.; Vakarov, Sergey A. [Organic and Biomolecular Chemistry, 2022, vol. 20, # 4, p. 862 - 869]
[2]Liu, Bin; Song, Runjiang; Xu, Jun; Majhi, Pankaj Kumar; Yang, Xing; Yang, Song; Jin, Zhichao; Chi, Yonggui Robin [Organic Letters, 2020, vol. 22, # 9, p. 3335 - 3338]

75
[ 6066-82-6 ]
[ 940-31-8 ]
2,5-dioxopyrrolidin-1-yl (RS)-2-phenoxypropanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 24h;
67%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere;

Reference： [1]Bartashevich, Ekaterina V.; Chulakov, Evgeny N.; Ezhikova, Marina A.; Gruzdev, Dmitry A.; Kodess, Mikhail I.; Korolyova, Marina A.; Krasnov, Victor P.; Levit, Galina L.; Tumashov, Andrey A.; Vakarov, Sergey A. [Organic and Biomolecular Chemistry, 2022, vol. 20, # 4, p. 862 - 869]
[2]Jin, Songyang; Geng, Xinxin; Li, Yujun; Zheng, Ke [European Journal of Organic Chemistry, 2021, vol. 2021, # 6, p. 969 - 972]

76
[ 940-31-8 ]
[ 106-49-0 ]
2‑phenoxy‑N‑(p‑tolyl)propanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With Candida antarctica lipase immobilized on acrylic resin In n-heptane at 80℃; for 72h; Molecular sieve; Green chemistry; Enzymatic reaction;	Enzymatic amidation of non-activated carboxylic acids General procedure: To a solution of 2 mmol amine and the 1 mmol carboxylic acid dissolved in 1 mL of heptane, 50 mg of the molecular sieves 4 and 50 mg of the immobilized CAL-B are introduced.The reaction mixture is stirred at 80 °C for 72 h. After cooling, the solvent is evaporated and the crude residue was exposed to a standard acido-basic treatment (HCl, 3 M / 3 M NaOH). The solvent was removed in vacuo, and the residue was crystallized in hexane, or purified by flash chromatography if necessary. As a control reaction, the same procedure is followed without introducing lipase. All the synthesized amides are characterized by 1H NMR, 13C NMR spectra and HRMS. Melting points were determined. Separation conditions on chiral HPLC were established. Optical rotations of proline amides 4a-5e were measured.

Reference： [1]Benamara, Nourelhouda; Merabet-Khelassi, Mounia; Aribi-Zouioueche, Louisa; Riant, Olivier [Chemical Papers, 2021, vol. 75, # 8, p. 4045 - 4053]

77
[ 455-14-1 ]
[ 940-31-8 ]
2‑phenoxy‑N‑(4‑(trifluoromethyl)phenyl)propanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With Candida antarctica lipase immobilized on acrylic resin In n-heptane at 80℃; for 72h; Molecular sieve; Green chemistry; Enzymatic reaction;	Enzymatic amidation of non-activated carboxylic acids General procedure: To a solution of 2 mmol amine and the 1 mmol carboxylic acid dissolved in 1 mL of heptane, 50 mg of the molecular sieves 4 and 50 mg of the immobilized CAL-B are introduced.The reaction mixture is stirred at 80 °C for 72 h. After cooling, the solvent is evaporated and the crude residue was exposed to a standard acido-basic treatment (HCl, 3 M / 3 M NaOH). The solvent was removed in vacuo, and the residue was crystallized in hexane, or purified by flash chromatography if necessary. As a control reaction, the same procedure is followed without introducing lipase. All the synthesized amides are characterized by 1H NMR, 13C NMR spectra and HRMS. Melting points were determined. Separation conditions on chiral HPLC were established. Optical rotations of proline amides 4a-5e were measured.

Reference： [1]Benamara, Nourelhouda; Merabet-Khelassi, Mounia; Aribi-Zouioueche, Louisa; Riant, Olivier [Chemical Papers, 2021, vol. 75, # 8, p. 4045 - 4053]

78
[ 940-31-8 ]
[ 540-37-4 ]
N‑(4‑iodophenyl)‑2‑phenoxypropanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With Candida antarctica lipase immobilized on acrylic resin In n-heptane at 80℃; for 72h; Molecular sieve; Green chemistry; Enzymatic reaction;	Enzymatic amidation of non-activated carboxylic acids General procedure: To a solution of 2 mmol amine and the 1 mmol carboxylic acid dissolved in 1 mL of heptane, 50 mg of the molecular sieves 4 and 50 mg of the immobilized CAL-B are introduced.The reaction mixture is stirred at 80 °C for 72 h. After cooling, the solvent is evaporated and the crude residue was exposed to a standard acido-basic treatment (HCl, 3 M / 3 M NaOH). The solvent was removed in vacuo, and the residue was crystallized in hexane, or purified by flash chromatography if necessary. As a control reaction, the same procedure is followed without introducing lipase. All the synthesized amides are characterized by 1H NMR, 13C NMR spectra and HRMS. Melting points were determined. Separation conditions on chiral HPLC were established. Optical rotations of proline amides 4a-5e were measured.

Reference： [1]Benamara, Nourelhouda; Merabet-Khelassi, Mounia; Aribi-Zouioueche, Louisa; Riant, Olivier [Chemical Papers, 2021, vol. 75, # 8, p. 4045 - 4053]

79
[ 940-31-8 ]
[ 106-40-1 ]
N‑(4‑bromophenyl)‑2‑phenoxypropanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With Candida antarctica lipase immobilized on acrylic resin In n-heptane at 80℃; for 72h; Molecular sieve; Green chemistry; Enzymatic reaction;	Enzymatic amidation of non-activated carboxylic acids General procedure: To a solution of 2 mmol amine and the 1 mmol carboxylic acid dissolved in 1 mL of heptane, 50 mg of the molecular sieves 4 and 50 mg of the immobilized CAL-B are introduced.The reaction mixture is stirred at 80 °C for 72 h. After cooling, the solvent is evaporated and the crude residue was exposed to a standard acido-basic treatment (HCl, 3 M / 3 M NaOH). The solvent was removed in vacuo, and the residue was crystallized in hexane, or purified by flash chromatography if necessary. As a control reaction, the same procedure is followed without introducing lipase. All the synthesized amides are characterized by 1H NMR, 13C NMR spectra and HRMS. Melting points were determined. Separation conditions on chiral HPLC were established. Optical rotations of proline amides 4a-5e were measured.

Reference： [1]Benamara, Nourelhouda; Merabet-Khelassi, Mounia; Aribi-Zouioueche, Louisa; Riant, Olivier [Chemical Papers, 2021, vol. 75, # 8, p. 4045 - 4053]

80
[ 940-31-8 ]
[ 106-47-8 ]
[ 335204-06-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	With Candida antarctica lipase immobilized on acrylic resin In n-heptane at 80℃; for 72h; Molecular sieve; Green chemistry; Enzymatic reaction;	Enzymatic amidation of non-activated carboxylic acids General procedure: To a solution of 2 mmol amine and the 1 mmol carboxylic acid dissolved in 1 mL of heptane, 50 mg of the molecular sieves 4 and 50 mg of the immobilized CAL-B are introduced.The reaction mixture is stirred at 80 °C for 72 h. After cooling, the solvent is evaporated and the crude residue was exposed to a standard acido-basic treatment (HCl, 3 M / 3 M NaOH). The solvent was removed in vacuo, and the residue was crystallized in hexane, or purified by flash chromatography if necessary. As a control reaction, the same procedure is followed without introducing lipase. All the synthesized amides are characterized by 1H NMR, 13C NMR spectra and HRMS. Melting points were determined. Separation conditions on chiral HPLC were established. Optical rotations of proline amides 4a-5e were measured.

Reference： [1]Benamara, Nourelhouda; Merabet-Khelassi, Mounia; Aribi-Zouioueche, Louisa; Riant, Olivier [Chemical Papers, 2021, vol. 75, # 8, p. 4045 - 4053]

81
[ 940-31-8 ]
[ 104-94-9 ]
[ 304690-04-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With Candida antarctica lipase immobilized on acrylic resin In n-heptane at 80℃; for 72h; Molecular sieve; Green chemistry; Enzymatic reaction;	Enzymatic amidation of non-activated carboxylic acids General procedure: To a solution of 2 mmol amine and the 1 mmol carboxylic acid dissolved in 1 mL of heptane, 50 mg of the molecular sieves 4 and 50 mg of the immobilized CAL-B are introduced.The reaction mixture is stirred at 80 °C for 72 h. After cooling, the solvent is evaporated and the crude residue was exposed to a standard acido-basic treatment (HCl, 3 M / 3 M NaOH). The solvent was removed in vacuo, and the residue was crystallized in hexane, or purified by flash chromatography if necessary. As a control reaction, the same procedure is followed without introducing lipase. All the synthesized amides are characterized by 1H NMR, 13C NMR spectra and HRMS. Melting points were determined. Separation conditions on chiral HPLC were established. Optical rotations of proline amides 4a-5e were measured.

Reference： [1]Benamara, Nourelhouda; Merabet-Khelassi, Mounia; Aribi-Zouioueche, Louisa; Riant, Olivier [Chemical Papers, 2021, vol. 75, # 8, p. 4045 - 4053]

82
[ 940-31-8 ]
[ 100-46-9 ]
[ 124371-71-7 ]

Yield	Reaction Conditions	Operation in experiment
64%	With Candida antarctica lipase immobilized on acrylic resin In n-heptane at 80℃; for 72h; Molecular sieve; Green chemistry; Enzymatic reaction;	Enzymatic amidation of non-activated carboxylic acids General procedure: To a solution of 2 mmol amine and the 1 mmol carboxylic acid dissolved in 1 mL of heptane, 50 mg of the molecular sieves 4 and 50 mg of the immobilized CAL-B are introduced.The reaction mixture is stirred at 80 °C for 72 h. After cooling, the solvent is evaporated and the crude residue was exposed to a standard acido-basic treatment (HCl, 3 M / 3 M NaOH). The solvent was removed in vacuo, and the residue was crystallized in hexane, or purified by flash chromatography if necessary. As a control reaction, the same procedure is followed without introducing lipase. All the synthesized amides are characterized by 1H NMR, 13C NMR spectra and HRMS. Melting points were determined. Separation conditions on chiral HPLC were established. Optical rotations of proline amides 4a-5e were measured.

Reference： [1]Benamara, Nourelhouda; Merabet-Khelassi, Mounia; Aribi-Zouioueche, Louisa; Riant, Olivier [Chemical Papers, 2021, vol. 75, # 8, p. 4045 - 4053]

83
[ 940-31-8 ]
[ 6638-79-5 ]
N-methoxy-N-methyl-2-phenoxypropionamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;

Reference： [1]Zhang, Chenhao; Gao, Anthony Z.; Nie, Xin; Ye, Chen-Xi; Ivlev, Sergei I.; Chen, Shuming; Meggers, Eric [Journal of the American Chemical Society, 2021, vol. 143, # 33, p. 13393 - 13400]

84
[ 87-86-5 ]
[ 940-31-8 ]
2,3,4,5,6-pentachlorophenyl (RS)-2-phenoxypropanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 24h;

Reference： [1]Bartashevich, Ekaterina V.; Chulakov, Evgeny N.; Ezhikova, Marina A.; Gruzdev, Dmitry A.; Kodess, Mikhail I.; Korolyova, Marina A.; Krasnov, Victor P.; Levit, Galina L.; Tumashov, Andrey A.; Vakarov, Sergey A. [Organic and Biomolecular Chemistry, 2022, vol. 20, # 4, p. 862 - 869]

85
[ 940-31-8 ]
3-(1-(benzyloxy)-2-phenoxypropyl)-1-azabicyclo[1.1.0]butane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 1,1'-carbonyldiimidazole / dichloromethane / 1 h / 0 °C / Inert atmosphere; Schlenk technique 1.2: 1 h / -78 °C / Inert atmosphere; Schlenk technique 2.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere; Schlenk technique 2.2: 1 h / -78 °C / Inert atmosphere; Schlenk technique 3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / 0 °C / Inert atmosphere; Schlenk technique 3.2: 16 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

Reference： [1]Aggarwal, Varinder K.; Noble, Adam; Tyler, Jasper L. [Angewandte Chemie - International Edition, 2022, vol. 61, # 3][Angew. Chem., 2022, vol. 134, # 3]

86
[ 940-31-8 ]
1-(1-azabicyclo[1.1.0]butan-3-yl)-2-phenoxypropan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / dichloromethane / 1 h / 0 °C / Inert atmosphere; Schlenk technique 1.2: 1 h / -78 °C / Inert atmosphere; Schlenk technique 2.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere; Schlenk technique 2.2: 1 h / -78 °C / Inert atmosphere; Schlenk technique

Reference： [1]Aggarwal, Varinder K.; Noble, Adam; Tyler, Jasper L. [Angewandte Chemie - International Edition, 2022, vol. 61, # 3][Angew. Chem., 2022, vol. 134, # 3]

87
[ 940-31-8 ]
[ 52687-81-7 ]

Yield	Reaction Conditions	Operation in experiment
44%	Stage #1: 2-phenoxypropionic acid With 1,1'-carbonyldiimidazole In dichloromethane at 0℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: With diisobutylaluminium hydride In dichloromethane; toluene at -78℃; for 1h; Inert atmosphere; Schlenk technique;

Reference： [1]Aggarwal, Varinder K.; Noble, Adam; Tyler, Jasper L. [Angewandte Chemie - International Edition, 2022, vol. 61, # 3][Angew. Chem., 2022, vol. 134, # 3]

88
[ 940-31-8 ]
tert-butyl 3'-(benzyloxy)-2'-methylspiro[azetidine-3,4'-chromane]-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: 1,1'-carbonyldiimidazole / dichloromethane / 1 h / 0 °C / Inert atmosphere; Schlenk technique 1.2: 1 h / -78 °C / Inert atmosphere; Schlenk technique 2.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere; Schlenk technique 2.2: 1 h / -78 °C / Inert atmosphere; Schlenk technique 3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / 0 °C / Inert atmosphere; Schlenk technique 3.2: 16 h / 0 - 20 °C / Inert atmosphere; Schlenk technique 4.1: tetrafluoroboric acid diethyl ether / chloroform / 1 h / 0 °C / Inert atmosphere; Schlenk technique 4.2: 16 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

Reference： [1]Aggarwal, Varinder K.; Noble, Adam; Tyler, Jasper L. [Angewandte Chemie - International Edition, 2022, vol. 61, # 3][Angew. Chem., 2022, vol. 134, # 3]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	940-31-8	MDL No. :	MFCD00002643
Formula :	C₉H₁₀O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SXERGJJQSKIUIC-UHFFFAOYSA-N
M.W :	166.17	Pubchem ID :	13658
Synonyms :

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	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

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 940-31-8 ] {[proInfo.proName]}

Quality Control of [ 940-31-8 ]

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Safety of [ 940-31-8 ]

Application In Synthesis of [ 940-31-8 ]

[ 940-31-8 ] Synthesis Path-Upstream 1~2

[ 940-31-8 ] Synthesis Path-Downstream 1~88

Related Functional Groups of
[ 940-31-8 ]

Aryls

Ethers

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

[ CAS No. 940-31-8 ] {[proInfo.proName]}

Quality Control of [ 940-31-8 ]

Related Doc. of [ 940-31-8 ]

Product Details of [ 940-31-8 ]

Safety of [ 940-31-8 ]

Application In Synthesis of [ 940-31-8 ]

[ 940-31-8 ] Synthesis Path-Upstream 1~2

[ 940-31-8 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 940-31-8 ]

Aryls

Ethers

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 940-31-8 ]