A Convenient Reductive Removal of Benzylic Hydroxyl and Trimethylsilyloxyl Groups with Me3SiCl–NaI–MeCN Reagent

Abstract

Secondary and tertiary hydroxyl groups at benzylic positions were reductively removed by treatment with 6 equivalents of Me₃SiCl–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 related compounds, as well as (±)-ar-turmerone, an odorous sesquiterpene.