Synfacts 2006(10): 1077-1077  
DOI: 10.1055/s-2006-949293
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

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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Publikationsverlauf

Publikationsdatum:
21. September 2006 (online)

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).