4-Cyanomandelic acid ethyl ester

Base Information

• Chemical Name: 4-Cyanomandelic acid ethyl ester
• CAS No.: 847227-46-7
• Molecular Formula: C11H11NO3
• Molecular Weight: 205.213
• Hs Code.: 2926909090
• Mol file: 847227-46-7.mol

Synonyms:4-CYANOMANDELIC ACID ETHYL ESTER

Chemical Property of 4-Cyanomandelic acid ethyl ester

Chemical Property:

• PSA: 70.32000
• LogP: 1.15478

Purity/Quality:

98%Min ^*data from raw suppliers

Ethyl2-(4-cyanophenyl)-2-hydroxyacetate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Cyanomandelic acid ethyl ester

There total 2 articles about 4-Cyanomandelic acid ethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

ethyl-4-cyanobenzoylformate (302912-31-8) → ethyl 2-(4-cyanophenyl)-2-hydroxyacetate (847227-46-7)

Guidance literature:

With sodium cyanoborohydride; acetic acid; In ethanol; water; at 20 ℃;

DOI:10.1021/ol100522z

Reference yield: 37.0%

glyoxylic acid ethyl ester (924-44-7) + 4-cyanophenylboronic acid (126747-14-6) → ethyl 2-(4-cyanophenyl)-2-hydroxyacetate (847227-46-7)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; caesium carbonate; johnphos; In toluene; at 80 ℃; for 23h; Inert atmosphere;

DOI:10.1002/ejoc.200800881

Reference yield: 94.0%

ethyl 2-(4-cyanophenyl)-2-hydroxyacetate (847227-46-7) + methanesulfonyl chloride (124-63-0) → ethyl 2-(4-cyanophenyl)-2-(methylsulfonyloxy)acetate (1221966-53-5)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ol100522z

upstream raw materials:

glyoxylic acid ethyl ester

4-cyanophenylboronic acid

ethyl-4-cyanobenzoylformate

Downstream raw materials:

ethyl 2-(4-cyanophenyl)-2-(methylsulfonyloxy)acetate

(R/S)-2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetamide

(R/S)-N-(2-(ethylamino)-2-oxoethyl)-2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetamide

(R/S)-N-ethyl-2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetamide

Refernces

• 1、 -. "4 - (5 - ISOXAZOLYL OR 5 - PYRRAZOLYL -1,2,4- OXADIAZOL - 3 - YL) -MANDELIC ACID AMIDES AS SPHINGOSIN- 1 - PHOSPHATE 1 RRECEPTOR AGONISTS". Page/Page column 68-69. . Retrieved 2011/11/06.
• 2、 Francesco, Irene Notar,Wagner, Alain,Colobert, Francoise. "Suzuki-Miyaura coupling reaction of boronic acids and ethyl glyoxylate: Synthetic access to mandelate derivatives". supporting information; experimental part. p. 5692 - 5695. Retrieved 2009/05/31.