| Abstract
| - Herein we report a very effective and mild procedure for the silylprotection of a wide variety ofsubstrate alcohols, including primary, secondary, allylic, propargylic,benzylic, hindered secondary,tertiary, acid-sensitive, and base-sensitive alcohols and also hinderedphenols. The silylation reagentused is tert-butyldimethylsilyl chloride (TBDMSCl) and thecatalyst is P(MeNCH2CH2)3N,1b, bothof which are commercially available. The reactions are carried outin acetonitrile from 24 to 40 °Cand on rare occasions in DMF from 24 to 80 °C. The effect ofsolvent, catalyst concentration, andtemperature and reaction time on the silylation of alcohols and theexcellent compatibility of ourmethod with a variety of functional groups is discussed. Anefficient method for recycling thecatalyst is also presented. Although representative primaryalcohols, secondary alcohols, andphenols were silylated using the more sterically hindered reagenttert-butyldiphenylsilyl chloride(TBDPSCl) in the presence of 1b as a catalyst, tertiaryalcohols were recovered unchanged.
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