PAPER	Synthesis 2005: 3035-3038   DOI: 10.1055/s-2005-916030
© Georg Thieme Verlag Stuttgart · New York
A Practical Preparation of 2-Hydroxymethyl-2-cyclopenten-1-one by Morita-Baylis-Hillman Reaction
Hisanaka Ito*, Yosuke Takenaka, Shouhei Fukunishi, Kazuo Iguchi*
School of Life Science, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan Fax: +81(426)767282; e-Mail: itohisa@ls.toyaku.ac.jp; e-Mail: onocerin@ls.toyaku.ac.jp;
Received 9 May 2005

Abstract

Tributylphosphine or dimethylphenylphosphine (1-5 mol%) catalyzed the Morita-Baylis-Hillman reaction of 2-cyclopenten-1-one (1) with 1.2 equivalents of formalin proceeded nicely to give 2-hydroxymethyl-2-cyclopenten-1-one (2) within a short period and in an excellent yield. The efficiency of the reaction (yield and time) was strongly dependent on the solvent and the best result was obtained in the case of an aqueous MeOH-CHCl₃ solvent system.

Key words

addition reactions - carbocycles - catalysis - enones - phosphorus