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Citation: CAI Xiao-Hua, XIE Bing. Synthesis of Ethyl(S)-2-Ethoxy-3-(4-hydroxyphenyl)propionate[J]. Chinese Journal of Applied Chemistry, ;2006, 23(9): 992-995. shu

Synthesis of Ethyl(S)-2-Ethoxy-3-(4-hydroxyphenyl)propionate

CAI Xiao-Hua ^a,b,, ,
XIE Bing ^b

1.
a Department of Pharmacy, HuaiHua Medical College, Huaihua 418000;
2.
b College of Chemistry and Environmental Science, Guizhou University for Nationalites, Guiyang

Corresponding author: CAI Xiao-Hua,
Received Date: 10 October 2005
Available Online: 10 March 2006
Fund Project: 湖南省教育厅青年科学基金资助项目(06C050) (06C050)

Ethyl(S)-2-ethoxy-3-(4-hydroxyphenyl)propionate(1) was prepared via a racemic synthetic route.Ethyl 2-chloride-2-ethoxyacetate(3) was synthesized from ethyl 2,2-diethoxyacetate(2) in a yield of 93%,which reacted with triethyl phosphate to give triethyl phosphonocetate(4) in a yield of 95%.Compound 4 was condensed with 4-benzyloxybenzaldehyd by Horner Wadswordth Emmons reaction to produce ethyl(Z,E)-2-ethoxy-3-(4-benzyloxy phenyl)propenonate(5) in a yield of 94%,which was hydrogenated to give ethyl(R,S)-2-ethoxy-3-(4-hydroxyphenyl) propionate(6) in a yield of 98%.The corresponding carboxylic acid(7) was obtained by the hydrolysis of compound 6 under basic conditions in a yield of 96%.Chemical resolution of compound 7 with chiral amine R-(α)-methyl benzamethanamine produced compound 8.The esterification of compound 8 produced product 1,and its yield and ee value were 95% and 98.3%,respectively.
- ethyl diethoxyacetate,
- Horner Wadswordth Emmons reaction,
- catalytic hydrogenation,
- chemical resolution,
- ethyl(S)-ethoxy-(hydroxyphenyl)propionate
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