A Practical Preparation of 2-Hydroxymethyl-2-cyclopenten-1-one by Morita-Baylis-Hillman Reaction

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 o...

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Veröffentlicht in:Synthesis (Stuttgart) 2005-11, Vol.2005 (18), p.3035-3038
Hauptverfasser: Ito, Hisanaka, Takenaka, Yosuke, Fukunishi, Shouhei, Iguchi, Kazuo
Format: Artikel
Sprache:eng
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Zusammenfassung: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-CHCl 3 solvent system.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2005-916030