2,3-bis((9Z,12Z)-octadeca-9,12-dienyloxy)propanal → (12Z,15Z)-1,2-bis((9Z,12Z)-octadeca-9,12-dienyloxy)henicosa-12,15-dien-3-ol

Participants

Reaction Steps

To a solution of 2,3-bis((9Z,12Z)-octadeca-9,12-dienyloxy)propanal (1.5 g, 2.62 mmol) in anhydrous diethyl ether (10 mL) was added LinMgBr Grignard (2.56 mL, 5.23 mmol). Upon completion, the solution was quenched with 5% HCl (50 mL) and washed with diethyl ether (3×50 mL). The combined ethyl ether extracts were dried on magnesium sulfate, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography on silica gel 60 (eluted with a gradient of 100% hexanes to 2% ethyl acetate in hexanes) to afford (12Z,15Z)-1,2-bis((9Z,12Z)-octadeca-9,12-dienyloxy)henicosa-12,15-dien-3-ol as a colorless oil (460 mg, 21%).

Provenance & Evidence