Synthesis

A convenient method of synthesizing 3-ethoxycarbonylbenzofurans from salicylaldehydes and ethyl diazoacetate

ME Dudley, MM Morshed, MM Hossain

Index: Dudley, Matthew E.; Morshed, M. Monzur; Hossain, M. Mahmun Synthesis, 2006 , # 10 p. 1711 - 1714

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Citation Number: 21

Abstract

In 2004, we reported a procedure for making 3-hydroxyacrylate 7 from ethyl diazoacetate and benzaldehyde (6) in excellent yield using HBF 4 ·OEt 2 as a catalyst (Scheme [1] ). [4] During our studies with substituted benzaldehydes to prepare substituted 3-hydroxyacrylates, we reacted salicylaldehyde (1a) with ethyl diazoacetate in the presence of HBF 4 ·OEt 2 . The reaction did not produce any acrylate 8, rather 20% of 3-ethoxycarbonylbenzofuran (2a) was isolated ...