Pyridine → (-)-Methyl jasmonate

Participants

Reaction Steps

Four hundred mg. of the methyl ester of 3-oxo-2-(2-pentynyl)-cyclopentaneacetic acid dissolved in 10 ml. of pyridine is added to 100 mg of 5% palladium on barium sulfate, and the resulting mixture is hydrogenated at room temperature and pressure. Forty-four milliliters of hydrogen is absorbed in 90 minutes, then the reaction stops completely. After filtering off the catalyst, the solvent is evaporated. The remaining oil is dissolved in ether-hexane 1:1 and washed with 1N HCl, aqueous saturated sodium bicarbonate and finally water. After drying (MgSO4), the solvent is evaporated and 392 mg. of methyl cis-jasmonate is obtained. Yield 98%. Spectral properties are in agreement with the above structure and published spectral data. The product shows one spot on thin layer chromatography. Methyl cis-jasmonate was also characterized as its semicarbazone, m.p. 118°-119° C (Lit. 115°-117° C).

Provenance & Evidence