An Efficient and Highly Chemoselective Method to Desilylate Silyl Ethers

Abstract

An efficient and highly chemoselective desilylating method is described. Trimethylsilyl ethers (0.25 M) in a CH3OH/CCl4 (1:1) solvent mixture are deprotected to their corresponding alcohols with ultrasound in a commercial ultrasonic cleaning bath. Selective deprotection of tert‐butyldimethylsilyl ethers of benzyl alcohols and phenols is achieved under ultrasonic conditions. We deprotected also tert‐butyldimethylsilyl ethers of primary alcohols, whereas tert‐butyldimethylsilyl ethers of secondary and tertiary alcohols are stable under these conditions.