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

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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… Click to show full 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.

Keywords: benzylidene acetals; acid promoted; methoxybenzyl ethers; lewis acid; acid scavenger

Journal Title: Organic letters
Year Published: 2023

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