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Synlett 2000; 2000(7): 1025-1027
DOI: 10.1055/s-2000-6676
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Facile O-Silylation of Tertiary Alcohols in the Presence of Mg-Metal

Ikuzo Nishiguchi* , Yoshio Kita, Masamitsu Watanabe, Yoshio Ishino, Toshinobu Ohno, Hirofumi Maekawa
  • *Department of Chemistry, Nagaoka University of Technology, 1603-1, Kamitomioka-cho, Nagaoka, Niigata 940-2188, Japan; Fax + 81-258-47-9300; E-mail: nishiiku@vos.nagaokaut.ac.jp
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Publikationsdatum:
31. Dezember 2000 (online)

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Treatment of aliphatic alcohols with trimethylsilyl chloride (TMSCl) in N,N-dimethylformamide (DMF) containing Mg-turning at room temperature brought about facile and efficient O-silylation to give the corresponding trimethylsilyl ethers in good to excellent yields. This method can be also available for sterically hindered tert-alcohols and alcohols having a variety of substituents which may be labile under the basic conditions used in the conventional O-silylation.

Mg-metal - O-silylation - tertiary alcohols - silyl ethers - trimethylsilyl chloride