Synlett 2003(6): 0825-0828
DOI: 10.1055/s-2003-38744
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Aryl, Alkyl bis-Silyl Ethers: Rapid Access to Monoprotected Aryl Alkyl and Biaryl Ethers

Sudha V. Ankala, Gabriel Fenteany*
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607-7061, USA
Fax: +1(312)9960431; e-Mail: fenteany@uic.edu;
Further Information

Publication History

Received 13 March 2003
Publication Date:
17 April 2003 (online)

Abstract

A simple one-pot procedure has been developed for the selective etherification of aryl silyl ethers in aryl, alkyl bis-silyl ethers to generate alkyl tert-butyldimethylsilyl-protected aryl alkyl ethers and biaryl ethers in good to excellent yields.

14

Preparation of 8 will be reported elsewhere.

15

It is noteworthy that the ester groups in both 7a and 7b remained intact after exposure to 3.0 equiv of LiOH/DMF at r.t. and the coupled product 9 could be obtained in excellent yields.