Improved Preparation of N-Trimethylsilylpyridinium Triflate, N-Triphenylsilylpyridinium Triflate, N-Triisopropylsilylpyridinium Triflate and Their Use in Silylating Alcohols to Silyl Ethers

George A. Olah; Douglas A. Klumpp

doi:10.1055/s-1997-1421

Synthesis 1997; 1997(7): 744-746
DOI: 10.1055/s-1997-1421

short paper

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Improved Preparation of N-Trimethylsilylpyridinium Triflate, N-Triphenylsilylpyridinium Triflate, N-Triisopropylsilylpyridinium Triflate and Their Use in Silylating Alcohols to Silyl Ethers

George A. Olah^* , Douglas A. Klumpp

^*Loker Hydrocarbon Research Institute, University of Southern California, Los Angeles, CA 90089-1661, USA, Fax +1(213)7406679

Abstract

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N-Silylpyridinium triflates 1a-c have been prepared in excellent yield from the corresponding allyl silanes by reaction with triflic acid followed by pyridine. Compounds 1a-c were used to prepare silyl ethers from alcohols in generally high yield. A convenient procedure has been developed which enables the silylation of alcohols without an aqueous workup in the product isolation.

N-silylpyridinium triflates - allylsilanes - silyl ethers - silylation - alcohols

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