[F:1][C:2]1[C:9]([CH:10]=[O:11])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1.FC1C=CC(C#N)=C(C(F)(F)F)C=1C=O.[BH4-].[Na+]>O1CCCC1.[Cl-].[Na+].O>[F:1][C:2]1[C:9]([CH2:10][OH:11])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:12]([F:13])([F:14])[F:15])[CH:3]=1
To a solution (15 mL) of a mixture (1.01 g) of 4-fluoro-5-formyl-2-(trifluoromethyl)benzonitrile and 4-fluoro-3-formyl-2-(trifluoromethyl)benzonitrile (3:1) in tetrahydrofuran was added sodium borohydride (400 mg) at 0° C., and the mixture was stirred at room temperature for 12 hr. Saturated brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate=5:1→1:4) to give the title compound as a yellow oil (yield: 456 mg).
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