Tetrahedron letters

Anomalous Ring Opening of N-aryl-2-oxazolidinones by Anhydrous Alkoxide: A Convenient Preparation of n-(alkoxyethyl)-2, 6-disubstituted Anilines

LW Fancher, RD Gless, RY Wong

Index: Fancher, L.W.; Gless, R.D.; Wong, R.Y. Tetrahedron Letters, 1988 , vol. 29, # 40 p. 5095 - 5098

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Citation Number: 6

Abstract

Abstract N-(2-Alkoxyethyl) anilines may be prepared by acylation of an N-unsubstituted aniline with 2-chloroethyl chloroformate, ring closure to oxazolidinone, ring opening with alkoxide under anhydrous conditions to a carbamic acid salt, and decarboxylation. This unexpected mode of ring opening is especially useful in the preparation of N-(2-alkoxyethyl)- 2, 6-disubstituted anilines.