Deprotection of silyl ethers using 2,3-dichloro-5,6-dicyano-p-benzoquinone
Abstract
In the presence of a catalytic amount of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), triethylsilyl (TES) and tert-butyldimethylsilyl (TBDMS) ethers are readily hydrolysed to the corresponding alcohols in MeCN–H2O (9 : 1) or tetrahydrofuran (THF)–H2O (9 : 1). TES ethers are cleaved to alcohols more easily than TBDMS ethers. tert-Butyldiphenylsilyl (TBDPS) ethers are stable under these reaction conditions.