Synlett 2004(6): 1077-1079  
DOI: 10.1055/s-2004-820045
LETTER
© Georg Thieme Verlag Stuttgart · New York

Cyanosilylation of Ketones Catalyzed by Quaternary Ammonium Salt and N-Oxide

Hui Zhoua, Fu-Xue Chena, Bo Qina, Xiaoming Feng*a, Guolin Zhangb
a Key Laboratory of Green Chemistry & Technology (Sichuan University), Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China
Fax: +86(28)85418249; e-Mail: xmfeng@scu.edu.cn;
b Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, P. R. China
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Publikationsverlauf

Received 14 February 2004
Publikationsdatum:
25. März 2004 (online)

Abstract

Dibenzyldimethyl ammonium bromide and triethanol­amine N-oxide catalyze the formation of cyanohydrin trimethylsilyl ethers of ketones in 80-99% yield.

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Typical Procedure: To a mixture of ketone (1.1 mmol), dibenzyldimethyl ammonium bromide (0.027 mmol) and triethanolamine N-oxide (0.027 mmol) in CH2Cl2 (0.5 mL) was added trimethylsilyl cyanide (2.2 mmol, 2 equiv.) at r.t. The reaction was monitored by TLC, and after the reaction period described in Table [4] , the reaction mixture was concentrated under reduced pressure and purified by silica gel column to give the pure product with Et2O-petroleum ether (1:100) as the eluent.