Process for the preparation of 2-alkyl cyclopent-2-enones

Details Process for the preparation of 2-alkyl cyclopent-2-enones Process for the preparation of 2-alkyl cyclopent-2-enones

1986-03-03

1987-06-16

Reamer, James H.

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

Organic compounds

Carboxylic acid esters

568341, 568346, 564454, 564455, 558432, 549322, 549323, 549326, 549524, C07C 6730

Patent

active

046737596

ABSTRACT:
A process for the preparation of 2-alkyl cyclopent-2-enones having the formula: ##STR1## wherein R is as defined hereinafter. An .alpha.-olefin having the formula CH.sub.2 .dbd.CH--CH.sub.2 R is oxidized to the corresponding epoxide. The epoxide is reacted with an alkylating agent having the formula Na.sup.+ [CH(COOR").sub.2 ].sup.-, wherein R" is an ethyl, an isopropyl, or an isobutyl radical. An .alpha.-carbalkoxy-.gamma.-alkyl lactone is obtained, which, through saponification and decarboxylation, yields a .gamma.-alkyl lactone having the formula: ##STR2## which is reacted with a protic acid, thereby obtaining, by cyclization, the desired 2-alkylcyclopent-2-enone. The obtained products are intermediates for the production of pharmaceutical products and of drugs for veterinary use, in particular prostaglandin.

REFERENCES:
patent: 3299100 (1967-01-01), Phillips
patent: 3755370 (1973-08-01), Fauran et al.
patent: 4138584 (1979-02-01), Klemmensen et al.
patent: 4229353 (1980-10-01), Klemmensen et al.
Eaton et al., J. Org. Chem., vol. 38, pp. 4071-4073 (1973).
DePuy et al., J. Org. Chem., vol. 29, p. 2810 (1964).
Venturello et al., J. Org. Chem., vol. 48, pp. 3831-3833 (1983).
Fieser et al., "Reagents for Organic Synthesis", pp. 135-137 (1967).

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