A New Method for the Preparation of 1-Ethynyl Ethers

Abstract

During our study of the stannylcupration of acetylenic ethers we required [2-13C]-1 for mechanistic studies. Existing methods for the synthesis of acetylenic ethers involve dehydrohalogenation of 2-halo, 1,2-dihalo vinyl ether, or haloacetals using KOH, NaNH2, or n-BuLi. These procedures are incompatible with labile functional groups and, if applied to the preparation of 13C-labeled compounds, would require regiospecific preparation of 1- or 2-13C-labeled halo vinyl ethers, which is cumbersome. We report a new, general and efficient method for the preparation of acetylenic ethers which we have applied to the preparation of 13C-labeled and functionalized acetylenic ethers