A Facile Synthesis of (E,Z)‐3‐Chloro‐2‐propenamides, Acids, and Esters from 2,3‐Acetylenic Acids with Oxalyl Chloride in DMF

Abstract

A simple route is described for the synthesis of E and Z 3‐chloro‐2‐propenamides (4a‐e), esters (3a) and acids (2a‐c) by the reaction of 2,3‐acetylenic acids with oxalyl chloride in DMF followed by treatment of the corresponding 3‐chloro‐2‐propenoyl chloride derivative with amines, alcohol and water.

Keywords:

• 2,3‐Acetylenic acids
• 3‐Chloro‐2‐alkenoic acids
• Hydrochlorination
• Oxalyl chloride
• DMF

Acknowledgments

The authors would like to thank the NMR Laboratory at the Chemistry Department‐Universidad Simón Bolívar (Proyect BID‐CONICIT QF‐13) and The National NMR Laboratory.