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Communication | Regular issue | Vol 85, No. 11, 2012, pp.2685-2691
Published online, 26th September, 2012
DOI: 10.3987/COM-12-12577
Application of SO3H Silica Gel to Deprotection of Silyl Ethers

Hideaki Fujii, Takaaki Yamada, Kohei Hayashida, Miki Kuwada, Atom Hamasaki, Kazunori Nobuhara, Sumio Ozeki, and Hiroshi Nagase*

*Laboratory of Medicinal Chemistry, School of Pharmacy, Kitasato University, 5-9-1, Shirokane, Minato-ku, Tokyo 108-8641, Japan

Abstract

A newly developed SO3H silica gel cleaved the O-Si bonds in various aryl and alkyl silyl ethers to give the corresponding phenols and alcohols in good to excellent yield. The crude filtrates contained no silyl residues. The solid phase 29Si NMR analyses of the SO3H silica gel strongly suggested that the silyl residues were captured by silanol groups on the surface of the silica gel. The SO3H silica gel could be recycled at least ten times without any loss of activity. The disappearance of silyl residues in the crude filtrate was observed in even the 10th repetition. Our method provides an easily handled desilylation method that requires no further purification. Our method was also applicable to a selective desilylation reaction of a derivative 5 with different siloxy groups or desilylation of an alkaloid derivative 7.