Chem. J. Chinese Universities ›› 1992, Vol. 13 ›› Issue (5): 630.

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Synthesis of 5-(2'-Carboxyethyl)-6-Alkyl-3,4-Dihydropyrone

HUANG Hua-min, LI Ye-zhi, REN Zhong-jao, XU Ya-qin   

  1. Department of Chemistry, Jilin University, Changchun, 130021
  • Received:1991-04-08 Online:1992-05-24 Published:1992-05-24

Abstract: 5-(2'-Carboxyethyl)-6-methyl-3,4-dihydropyrone(2a) and 5-(2'-carboxyethyl)-6-isobutyl-3,4-dihydropyrone (2c) were prepared from 4-acetyl heptanedioic acid (1a) and 4-iso-valeryl hyptanedioic acid (1c) in the presence of acetic anhydride with yields of 63%, 68% respectively.When 1c was refluxed with ferric sulfate hydrate as the catalyst product 2c also formed in 63% yield.2a,c or 5-(2'-carboxyethyl)-6-isopropyl-3, 4-dihydropyrone (2b) reacted with ethyl alcohol to afford 4-acylheptanedioic acid diethyl ester (3a-c) in the presence of hydrochlo-ride.Treatment of 2a-c with ammonia water gave 5-(2'-carboxyethyl)-6-alkyl-3, 4-dihydro pyridone (4a-c) in 55%~72% yields.

Key words: 4-Acylheptanedioic acid diethyl ester, 5-(2'-Carboxyethyl)-6-alkyl-3,4-dihydropy-rone, 5-(2'-Carboxyethyl)-6-alkyl-3,4-dihydropyridone

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