Triethylamine → Methyl dihydrojasmonate, cis-(+)-

Participants

Reaction Steps

To a solution of 252 mg (1.20 mmole) 3-oxo-2-pentyl-1 cyclopentene-1-acetic acid, in a mixture of 7 ml of THF and 21 ml of methanol, there were added 2 ml of the catalyst solution obtained in a) (0.025 mmole, 0.021 eq.) and 10.4 μl of triethylamine (0.075 mmole, 3 eq.) under stirring at r.t. This solution, prepared in the glass container of a standard autoclave, was introduced in this autoclave, which was locked, put under a pressure of 45×105Pa of hydrogen and stirred at r.t. The reaction was followed by gas chromatography and was completed in about 4 h. After 1 night, the contents were evaporated under vacuum at r.t., the residue taken in ether, washed with HCl 10.1N and then water, dried over MgSO4 and filtered. The thus obtained (+)-(1R)-3-oxo-2-pentyl-1-cyclopentaneacetic acid was esterified by means of diazomethane to yield methyl (+)-(1R)-cis-3-oxo-2-pentyl-1-cyclopentaneacetate, the chromatographic analysis (GC) of which indicated 97% purity, 96:4 cis/trans ratio and 95:5 (+)-(1R)-cis/(-)-(1S)-cis ratio.

Provenance & Evidence