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An Efficient and Highly Chemoselective Method to Desilylate Silyl Ethers
Author(s) -
Lee Adam ShihYuan,
Yeh HsiuChih,
Yeh MingKuo,
Tsai MingHung
Publication year - 1995
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199500126
Subject(s) - chemistry , silylation , trimethylsilyl , phenols , organic chemistry , solvent , primary (astronomy) , tertiary alcohols , ultrasonic sensor , alcohol , catalysis , physics , astronomy , acoustics
Abstract An efficient and highly chemoselective desilylating method is described. Trimethylsilyl ethers (0.25 M) in a CH 3 OH/CCl 4 (1:1) solvent mixture are deprotected to their corresponding alcohols with ultrasound in a commercial ultrasonic cleaning bath. Selective deprotection of tert‐butyldimethylsilyl ethers of benzyl alcohols and phenols is achieved under ultrasonic conditions. We deprotected also tert ‐butyldimethylsilyl ethers of primary alcohols, whereas tert ‐butyldimethylsilyl ethers of secondary and tertiary alcohols are stable under these conditions.