Sodium Chloride → HCID 19805831, compound

Participants

Reaction Steps

In 6 ml of dried THF, 585 mg (3.36 mmol) of the substrate (-)-2-fluoro-9-decen-1-ol was dissolved, and the solution was kept ice-cooled. Into the resulting solution, diborane prepared by dropwise adding 0.78 g (5.5 mmol) of a boron trifluoride ether complex to a 6 ml dried diglyme solution of 189 mg (5 mmol) of sodium borohydride was blown (for about 10 minutes). With further stirring at room temperature, the reaction mixture turned into a gel with progress of the reaction. After it was left to stand for 30 minutes, 0.5 ml of distilled water was dropwise added, followed by addition of 3 ml of an aqueous 3N sodium hydroxide solution and 3 ml of 30% hydrogen peroxide water. The reaction mixture was stirred for 30 minutes, sodium chloride was added, and the organic layer was taken out. Extraction from the aqueous layer was carried out twice using 2 ml of ethyl ether, and the extract was dried with anhydrous magnesium sulfate together with the organic layer previously taken out, followed by micro-distillation to give 493 mg (2.56 mmol) of 2-fluoro-1,10-decanediol. (0.7 torr, 170° to 190° C., 76% yield)

Provenance & Evidence