Mild deprotection of 2-(trimethylsilyl)ethyl esters

Authors
Serrano-Wu, MH Regueiro-Ren, A St Laurent, DR Carroll, TM Balasubramanian, BN
Citation
Mh. Serrano-wu et al., Mild deprotection of 2-(trimethylsilyl)ethyl esters, TETRAHEDR L, 42(49), 2001, pp. 8593-8595
Citations number
5
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
49
Year of publication
2001
Pages
8593 - 8595
Database
ISI
SICI code
0040-4039(200112)42:49<8593:MDO2E>2.0.ZU;2-Y
Abstract
A method for the deprotection of 2-(trimethylsilyl)ethyl (TMSE) esters is d escribed. Treatment of carboxylic esters with NaH in DMF cleanly produces t he deprotected acid after extractive work-up. This method can be applied to sterically-hindered substrates as well as esters containing fluoride-labil e functionality. A tandem alkylation/ester deprotection procedure is also p resented. (C) 2001 Published by Elsevier Science Ltd.