3-(2,3-二氢苯并呋喃-5-基)丙酸合成工艺的改进

An improved synthesis of 3-(2,3-dihydrobenzofuran-5-yl)propanoic acid

目的研究3-(2,3-二氢苯并呋喃-5-基)丙酸的实用合成方法。方法以3-(4-羟基苯基)丙烯酸为起始原料,甲酯化后依次与2-溴乙醛缩二乙醇缩合、Friedel-Crafts反应得3-(苯并呋喃-5-基)丙烯酸甲酯,再经10%Pd/C催化氢化和水解反应,得3-(2,3-二氢苯并呋喃-5-基)丙酸。结果 3-(2,3-二氢苯并呋喃-5-基)丙酸的化学结构经1HNMR和ESI-MS确证,总收率为60%。结论本合成方法与文献法比较,具有原料易得、反应条件温和、操作简便、收率高等优点。

OBJECTIVE To investigate a practical and convenient process for the synthesis of 3-（2,3-dihydrobenzofuran-5-yl） propanoic acid.METHODS 3-（2,3-Dihydrobenzofuran-5-yl） propanoic acid was synthesized by methyl esterification of 3-（4-hydroxyphenyl） acrylic acid,followed by condensation with bromoacetaldehyde diethyl acetal and Friedel-Crafts reaction to give methyl 3-（benzofuran-5-yl） acrylic acid,which was subsequently subjected to catalytic hydrogenation in the presence of 10% Pd/C and hydrolysis to afford 3-（2,3-dihydrobenzofuran-5-yl） propanoic acid.RESULTS The chemical structure of 3-（2,3-dihydrobenzofuran-5-yl） propanoic acid was determined by ~1HNMR and ESI-MS.The overall yield was 60%.CONCLUSION This process,as compared to the previously reported methods,has advantages of milder reaction condition,simpler operation and high yield.