Synthesis 2006(10): 1575-1577  
DOI: 10.1055/s-2006-926461
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

Efficient Two-Step Synthesis of Salicylaldehydes via Directed ortho-Lithiation of in situ N-Silylated O-Aryl N-Isopropylcarbamates

Matthias Kauch, Dieter Hoppe*
Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstraße 40, 48149 Münster, Germany
Fax: +49(251)8336531; e-Mail: dhoppe@uni-muenster.de;
Further Information

Publication History

Received 23 December 2005
Publication Date:
08 May 2006 (online)

Abstract

O-Aryl N-isopropylcarbamates, conveniently prepared from phenols and isopropyl isocyanate, are subjected to an efficient ortho-lithiation protocol to afford the corresponding salicylaldehydes in a one-pot operation in high yields.

19

Carbamate 1d can either be obtained by ortho-lithiation [8b] or by reaction of 2-(trimethylsilyl)phenol with isopropyl isocyanate (96%).