Deprotection of tert-Butyldimethysilyl Ethers Using Silica-Supported NaHSO4

B. Das; K. R. Reddy; P. Thirupathi

doi:10.1055/s-2006-949293

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Synfacts 2006(10): 1077-1077
DOI: 10.1055/s-2006-949293

Polymer-Supported Synthesis

Deprotection of tert-Butyldimethysilyl Ethers Using Silica-Supported NaHSO₄

Contributor(s): Yasuhiro Uozumi, Toshimasa Suzuka
B. Das*, K. R. Reddy, P. Thirupathi
Indian Institute of Chemical Technology, Hyderabad, India

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Publication History

Publication Date:
21 September 2006 (online)

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Significance

A simple method for deprotection of tert-butyldimethylsilyl (TBDMS) ethers using silica-supported sodium hydrogen sulfate was developed. Thus, silica-supported sodium hydrogen sulfate (1) was prepared according to the reported procedures (G. W. Breton J. Org Chem. 1997, 62, 8952-8954). The TBDMS ethers 2, prepared from both primary and secondary alcohols, underwent deprotection with 1 in CH₂Cl₂ to give the corresponding alcohols 3a-m (13 examples, 89-94% yield).