Process for preparing cyclopentenolones

Details Process for preparing cyclopentenolones Process for preparing cyclopentenolones

1981-04-22

1982-08-31

Trousof, Natalie

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

Organic compounds

Oxygen containing

568341, C07C 4567

Patent

active

043473865

ABSTRACT:
A process for preparing cyclopentenolones in good yields which comprises treating a 4-hydroxy-4-R.sub.2 -5-R.sub.1 -2-cyclopentenone of the formula: ##STR1## wherein R.sub.1 is an alkyl group having not more than 6 carbon atoms, an alkenyl group having not more than 6 carbon atoms, an alkynyl group having not more than 6 carbon atoms or a group of the formula: ##STR2## (in which R.sub.3 is hydrogen, methyl or halogen) and R.sub.2 is a hydrogen atom or a methyl group, provided that when R.sub.2 is hydrogen, R.sub.1 is neither .alpha.-methylallyl nor .alpha.-methylpropargyl, in an aqueous medium in the presence or absence of a metal salt at a temperature of 20.degree. to 200.degree. C. to give the corresponding 2-R.sub.1 -3-R.sub.2 -4-hydroxy-2-cyclopentenone of the formula: ##STR3## wherein R.sub.1 and R.sub.2 are each as defined above.

REFERENCES:
patent: 3932510 (1976-01-01), Muller
patent: 3932511 (1976-01-01), Muller
patent: 3981920 (1976-09-01), Buchi
patent: 4234516 (1980-11-01), Koller et al.
J. Am. Chem. Soc., Stork et al., "A Route to Prostaglandins via a General Synthesis of 4-Hydroxycyclopentenones", 97, pp. 3258-3260, (1975).
Synthesis, Piancatelli et al., "A Simple Conversion of 4-Substituted 5-Hydroxy-3-oxocyclopentenes into the 2-Substituted Analogs", pp. 116-117 (1976).
Tetrahedron letters, Piancatelli et al., "A Useful Preparation of 4-Substituted 5-Hydroxy-3-oxocyclopentene", 39, pp. 3555-3558 (1976).
Amgew Chem., Seebach et al., 4-Hydroxy-2-cyclopenten-1-one aus Ketonen und 3-Nitropropionylchlorid, E ine eintache Methode zum Aufbau von Funfrangen, 89, pp. 334-335 (1977).
Tetrahedron Letters, Piancatelli et al., "A Useful Preparation of (.+-.) T-Butyl 3-Hydroxy-5-Oxo-1-Cyclopentene-Heptanoate and Its 3-Deoxy-Derivative, Important Prostaglandin Intermediates," 13, pp. 1131-1134 (1977).
Tetrahedron, Piancatelli et al., "A New Synthesis of 3-Oxocyclopentenes," 34, pp. 2775-2778, (1978).
J. Org. Chem., Floyd, "Prestaglandins and Congeners". 18. Synthesis of Cyclopentenalone, Precurosors to Prostaglandins from 2-5-Oihyoro-2, 5-dimethoxyfurons, 43, pp. 1641-1643 (1978).
Tetrahedron, Piancatelli et al., "General Route and Mechanism Of The Rearrangement Of The 4-Substituted 5-Hydroxy-3-Oxocyclopentenes Into The 2-Substituted Analogs", 35, pp. 135-138. (1979).
Piancatelli et al., Tetrahedron, vol. 36, pp. 661-663, (1980).

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