A convenient reductive removal of benzylic hydroxyl and trimethylsilyloxyl groups with Me3SiCl-NaI-MeCN reagent.

T Sakai, K Miyata, S Tsuboi, A Takeda…

Index: Sakai; Miyata; Tsuboi; Takeda; Utaka; Torii Bulletin of the Chemical Society of Japan, 1989 , vol. 62, # 11 p. 3537 - 3541

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Citation Number: 27

Abstract

Secondary and tertiary hydroxyl groups at benzylic positions were reductively removed by treatment with 6 equivalents of Me 3 SiCl–NaI–MeCN reagent in hexane at room temperature. A benzylic trimethylsilyloxyl group was also eliminated by the addition of 2 equivalents of water to the reaction system. The reduction was applied to the syntheses of precursors of such anti-inflammatory agents as ibuprofen, butibufen, naproxen, and ...