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

TY - JOUR

T1 - Lewis Acid Promoted Deprotection of Benzylidene Acetals and p-Methoxybenzyl Ethers with Mercaptoacid Acid as Scavenger

AU - Greve, Rasmus D.

AU - Jensen, Henrik H.

PY - 2023/5

Y1 - 2023/5

N2 - We demonstrate a new and high-yielding method for removal of benzylidene acetals and para-methoxybenzyl ethers under catalytic conditions (BF3:OEt2orFeCl3, 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.

AB - We demonstrate a new and high-yielding method for removal of benzylidene acetals and para-methoxybenzyl ethers under catalytic conditions (BF3:OEt2orFeCl3, 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.

UR - http://www.scopus.com/inward/record.url?scp=85160457110&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.3c00958

DO - 10.1021/acs.orglett.3c00958

M3 - Letter

C2 - 37191475

AN - SCOPUS:85160457110

SN - 1523-7060

VL - 25

SP - 3628

EP - 3632

JO - Organic Letters

JF - Organic Letters

IS - 20

ER -