Sodium borohydride → HCID 66779033, compound

Reaction equation

[CH:1]1([C:7]([C:9]2[O:10][C:11]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:12]=3[C:13]=2[CH3:14])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+]>O1CCCC1.CO>[CH:1]1([CH:7]([C:9]2[O:10][C:11]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:12]=3[C:13]=2[CH3:14])[OH:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Procedure

Cyclohexyl(4-fluoro-3-methyl-1-benzofuran-2-yl)methanone (2.6 g) synthesized in the above-mentioned (1) was dissolved to in tetrahydrofuran (40 mL) and methanol (4 mL), and sodium borohydride (90%, 0.83 g) was added to the solution under ice-cooling. The ice bath was removed, the reaction mixture was stirred at room temperature for 1 hr then ice-cooled again, and water (5 mL) and 1N hydrochloric acid (10 mL) were carefully added to the mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio) to give the title object compound (2.5 g, quantitative) as a pale-yellow oil.