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Synlett 2006(8): 1260-1262  
DOI: 10.1055/s-2006-926256
LETTER
© Georg Thieme Verlag Stuttgart · New York

Facile Cleavage of Silyl Protecting Groups with Catalytic Amounts of FeCl3

Yong-Qing Yang, Jia-Rong Cui, Lin-Gui Zhu, Ya-Ping Sun, Yikang Wu*
State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. of China
Fax: +86(21)64166128; e-Mail: yikangwu@mail.sioc.ac.cn;
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Publication History

Received 4 September 2005
Publication Date:
10 March 2006 (online)

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Abstract

A very mild and environmentally benign method for ­removal of silyl protecting groups using catalytic amounts of iron ion in MeOH is presented. The method is particularly effective for cleaving triethylsilyl (TES) protecting groups.

Key words

deprotection - hydrolysis - removal - cleavage - iron ion

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General Procedure for Cleavage of Silyl Protecting Groups.
A solution of the substrate (ca. 0.3 M) in MeOH containing the indicated amount of FeCl3 was stirred at the ambient temperature (ca. 23 °C). The progress of the reaction was monitored with TLC. When the cleavage of the silyl protecting groups was complete, the reaction mixture was filtered through a short pad of silica gel to remove the inorganic salt (eluting with EtOAc). The filtrate and effluent were combined and concentrated on a rotary evaporator and the residue was purified by column chromatography on silica gel to give the product.