[BH4-].[Na+].[C:3]1([C:9]2[O:10][CH:11]=[C:12]([CH2:14][O:15][C:16]3[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=3)[N:13]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CO.Cl>O>[C:3]1([C:9]2[O:10][CH:11]=[C:12]([CH2:14][O:15][C:16]3[CH:17]=[CH:18][C:19]([CH2:20][OH:21])=[CH:22][CH:23]=3)[N:13]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1Sodium borohydride (0.36 g) was added to a mixture of 4-(2-phenyl-4-oxazolylmethoxy)benzaldehyde (2.65 g) and methanol (50 ml) under ice-cooling, which was stirred at room temperature for 1 hour. Dilute hydrochloric acid and water were added to the reaction mixture, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4) and concentrated to obtain 4-(2-phenyl-4-oxazolylmethoxy)benzyl alcohol (2.43 g, yield 91%) as colorless crystals. This was recrystallized from ethyl acetate-hexane. Melting point: 141–142° C.
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