Process for the preparation of bicyclic diketone salts

C - Chemistry – Metallurgy – 07 – C

Patent

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C07C 49/627 (2006.01) C07C 45/51 (2006.01) C07C 45/57 (2006.01) C07C 45/60 (2006.01) C07C 49/433 (2006.01) C07C 49/443 (2006.01) C07C 49/647 (2006.01) C07C 49/733 (2006.01) C07D 311/00 (2006.01) C07D 313/06 (2006.01)

Patent

CA 2424754

The present invention relates to a process for the preparation of bicyclic 1,3- diketone salts of formula I (see formula I), wherein R1, R2, R3 and R4 are each independently of the others hydrogen or C1- C4alkyl; A and E are each independently of the other C1-C2alkylene, which may be substituted once or up to four times by a C1-C4alkyl group, and M+ is an alkali metal ion, alkaline earth metal ion or ammonium ion, by oxidation of a compound of formula II (see formula II), to a compound of formula III (see formula III), and subsequent conversion to a compound of formula I either in the presence of a base and a catalytic amount of a cyanide or in the presence of an alkali metal alcoholate or alkaline earth metal alcoholate, and to novel bicyclic enol lactone intermediates of formula III for use in that process.

La présente invention concerne un procédé pour la préparation de sels 1,3-dicétobicycliques de formule I (voir la formule I), où R1, R2, R3 et R4 sont, indépendamment les uns des autres, un hydrogène ou un alkyle en C1 à C4; A et E sont, indépendamment l'un de l'autre, un alkylène en C1 ou C2, lequel peut compter jusqu'à 4 substituants alkyliques de 1 à 4 carbones; M+ est un ion de métal alcalin, un ion de métal alcalino-terreux ou un ion ammonium, par oxydation d'un composé de formule II (voir la formule II) pour obtenir un composé de formule III (voir la formule III)), et oxydation subséquente, pour obtenir un composé de formule I, soit en présence d'une base et d'une quantité catalytique de cyanure, soit en présence d'un alcoolate de métal alcalin ou d'un alcoolate de métal alcalino-terreux; l'invention a également trait à de nouveaux intermédiaires lacto-énoliques bicycliques de formule III utilisés dans ce procédé.

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