A Mild, Efficient, Inexpensive, and Selective Cleavage of Primary tert-Butyldimethylsilyl Ethers by Oxone in Aqueous Methanol

The use of a 50% aqueous methonolic solution of Oxone is described for the selective cleavage of primary tert -butyldimethylsilyl and aryl ethers at room temperature. This method enables one to deprotect tert -butyldimethylsilyl ethers of primary alcohols in the presence of tert -butyldimethylsilyl ethers of secondary and tertiary alcohols and phenols. The silyl ethers of phenols were deprotected at longer reaction times.