Process for preparing cyclopropyl alkyl ketones and 4,5-dihydroa

Details Process for preparing cyclopropyl alkyl ketones and 4,5-dihydroa Process for preparing cyclopropyl alkyl ketones and 4,5-dihydroa

1996-01-23

1997-05-13

Dentz, Bernard

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

549507, C07C 4554, C07D30728

Patent

active

056294557

ABSTRACT:
The invention relates to a novel process for the simultaneous preparation of cyclopropyl alkyl ketones and 4,5-dihydroalkylfurans from 3-acyltetrahydrofuran-2-ones using a metal salt according to the diagram ##STR1## In the reaction, N-alkyllactams and/or N-acylmorpholines which are high-boiling and only slightly miscible with water are used. By charging the solvent, the metal salt and the 3-acyltetrahydrofuran-2-one in a molar excess with respect to the metal salt, heating the mixture to 160.degree. to 220.degree. C. and metering in further 3-acyl-tetrahydrofuran-2-one, the desired products are obtained in high yields. The metal salt can moreover be recovered in a simple manner by washing with water.

REFERENCES:
Chemistry Letters, vol. 11, pp. 1149-1152, 1975, M. Asaoka, et al., "Alkylation Reaction Accompanied by Dealkoxycarbonylation of Beta-Keto Esters, Geminal Diesters and Alpha-Cyano Ester in Hexamethylphosphoric Triamide (HMPA)".
Tetrahedron Letters, vol. 49, pp. 4389-4392, 1975, S. Takei, et al., "A Novel Synthesis of Cyclopropyl Ketones Via Decarboxylative Ring Contractions of .alpha.-Acyl-.gamma.-butyrolactones Catalyzed by Halide Ions in Dipolar Aprotic Solvents".

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