Manufacture of 2-(alkyl, alkenyl or alkynyl) 3-carbalkoxyalkyl ketones from alpha, beta-unsaturated ketones
US4143230A · kind A · utility
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11Claims
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Key dates
| Filing date | Oct 28, 1976 |
| Grant date | Mar 6, 1979 |
| Priority date | — |
| Expiry date | Oct 28, 1996 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07C51/34
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
The copper enolate of 3-allylcyclopentanone is alkylated with an alkyne so as to form the 2-alkynyl, 3-allylcyclopentanone which is then subjected to ozonolysis and oxidative cleavage to form 2-alkynylcyclopentan-3-one-1-yl alkylcarboxlic acid. The acid can be esterified to form a 2-alkynyl-3-carbalkoxyalkyl ketone which, in turn, can be hydrogenated to convert the alkynyl moiety to alkenyl or alkyl moieties. The procedure is particularly useful in the synthesis of methyl dl-jasmonate, dehydrojasminate and dihydrojasmonate.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.