The Journal of organic chemistry

Propargyl bromide as an excellent α-bromoacetone equivalent: Convenient and new route to α-aroylacetones

SM Mahalingam, IS Aidhen

Index: Mahalingam, Sakkarapalayam M.; Aidhen, Indrapal Singh Journal of Organic Chemistry, 2006 , vol. 71, # 1 p. 349 - 351

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Citation Number: 12

Abstract

A variety of α-aroylacetones 4a-g have been prepared in excellent yields following a new protocol wherein α-aminonitriles 1a-g as the aryl acyl anion equivalents readily react with propargyl bromide as the α-bromoacetone equivalent. The alkylated product undergoes one- pot unmasking of the keto functionality along with Markovnikov's hydration of the terminal alkyne with CuSO4⊙ 5H2O in aqueous methanol at 60° C to furnish the desired target in ...