10-Bromo-1-decene → Octadeca-1,17-dien-8-one

Participants

Reaction Steps

A Grignard solution was prepared under nitrogen from 2.15 g (8.53 mmol) of 10-bromodec-1-ene and 249 mg (10.22 mmol) of magnesium powder in 20 mL of diethyl ether. The fresh Grignard solution was slowly added dropwise under a N2 atmosphere at 0° C. to a solution of 790 mg (4.26 mmol) of the methoxymethyl amide of oct-7-enoic acid and 10 mL of diethyl ether. Stirring was then continued at 20° C. for one hour. The charge was carefully quenched with Na4Cl solution and then extracted twice with diethyl ether. The organic phase was again washed with water, dried and concentrated. Column chromatographic fractionation furnished 820 mg (3.11 mmol) of octadeca-1,17-dien-8-one.

Provenance & Evidence