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Original Articles

EFFECTIVE SILYLATION OF CARBOXYLIC ACIDS UNDER SOLVENT-FREE CONDITIONS WITH tert-BUTYLDIMETHYLSILYL CHLORIDE (TBDMSCL) AND TRIISOPROPYLSILYL CHLORIDE (TIPSCL)

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Pages 71-81 | Received 04 Apr 2000, Accepted 06 Jun 2000, Published online: 19 Dec 2006
 

Abstract

Various types of carboxylic acids can be converted effectively to their corresponding TBDMS and TIPS esters using TBDMSCI and TIPSCI in the presence of imidazole under solvent-free conditions. The advantage of this modified method in comparison with that reported by Corey is the elimination of DMF, which eliminates aqueous work-up. The method is not a time-consuming process and the reactions proceed spontaneously. By this method, absolute chemoselectivity for the protection of carboxylic acid functions in the presence of 2°, 3° hydroxyl groups are observed.

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