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Synthesis 2005(18): 3035-3038
DOI: 10.1055/s-2005-916030
DOI: 10.1055/s-2005-916030
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Practical Preparation of 2-Hydroxymethyl-2-cyclopenten-1-one by Morita-Baylis-Hillman Reaction
Further Information
Received
9 May 2005
Publication Date:
06 October 2005 (online)
Publication History
Publication Date:
06 October 2005 (online)
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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
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