[CH2:1]([O:8][N:9]=[C:10]([C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=[O:16])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO.O1CCCC1>[CH2:1]([O:8][N:9]=[C:10]([C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15][OH:16])[CH3:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1To a solution of 9.92 g (39.17 mmol) of 3-(1-(benzyloxyimino)ethyl)benzaldehyde in 70 ml of dry methanol and 70 ml of dry tetrahydrofuran was added 1.81 g (43 mmol) of sodium borohydride portionwise with ice-cooling, and the mixture was stirred for 2 hours with ice-cooling. Further, 0.30 g of sodium borohydride portionwise was added thereto with ice-cooling, and the mixture was stirred for 2 hours with ice-cooling. The reaction mixture was poured into 500 ml of an about 5% aqueous solution of ammonium chloride, and the mixture was extracted with tert-butyl methyl ether. The organic layer was dried and concentrated to obtain 9.64 g (37.8 mmol) of 3-(1-(benzyloxyimino)ethyl)benzylalcohol.
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