Lewis Acid Promoted Deprotection of Benzylidene Acetals and p-Methoxybenzyl Ethers with Mercaptoacid Acid as Scavenger

Org Lett. 2023 May 26;25(20):3628-3632. doi: 10.1021/acs.orglett.3c00958. Epub 2023 May 16.

Abstract

We demonstrate a new and high-yielding method for removal of benzylidene acetals and para-methoxybenzyl ethers under catalytic conditions (BF3:OEt2 orFeCl3, 10 mol%) with mercaptoacetic acid as a scavenger. The reaction coproducts are converted to water-soluble molecules, which can be removed by aqueous extraction, thereby bypassing the need for chromatographic purification. The reaction was demonstrated on both multimilligram and multigram scale.