Sodium Chloride → Docosa-1,3,5,7,9,11-hexaen-1-ol

Participants

Reaction Conditions

Reaction Steps

1.28 g (33.7 mmol) of lithium aluminum hydride (LiAlH4) and 100 ml of anhydrous dietylether were placed into an eggplant-shape flask of which air had been replaced by argon gas, and kept at 0° C. To the mixture was added dropwise over about 30 minutes the solution of 10 g (28.1 mmol) of ethyl docosahexaenate in diethylether (20 ml of anhydrous diethylether), and then stirred at 0° C. for 30 minutes. After stirring, ethyl acetate and the saturated solution of sodium chloride were added to the reaction mixture, followed by removal of the precipitate by filtration. The filtrate was concentrated under reduced pressure, and purified by silica gel open column chromatography (hexane:ethyl acetate=5:1), to give 5.67 g of docosahexaenol (abbreviated as DHA-OH somewhere hereinafter).

Provenance & Evidence