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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, Email:

H. Ito, Y. Takenaka, S. Fukunishi, K. Iguchi, Synthesis, 2005, 3035-3038.

DOI: 10.1055/s-2005-916030


Tributylphosphine or dimethylphenylphosphine catalyzed the Morita-Baylis-Hillman reaction of 2-cyclopenten-1-one with 1.2 equivalents of formalin to give 2-hydroxymethyl-2-cyclopenten-1-one within a short period and in an excellent yield. The efficiency of the reaction was strongly dependent on the solvent system.

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Key Words

addition reactions, carbocycles, catalysis, enones, phosphorus, Baylis-Hillman Reaction

ID: J66-Y2005-1960