[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]([CH2:15][N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)[CH2:12][CH:13]=[O:14])[CH:7]=[CH:8][C:9]=1[Cl:10].Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]([CH2:15][N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)[CH2:12][CH2:13][OH:14])[CH:7]=[CH:8][C:9]=1[Cl:10]
Sodium borohydride (0.52 g) was added in three portions, over 5 minutes, to an ice-cooled solution of 3-(3,4-dichlorophenyl)-4-(imidazol-1-yl)butan-1-al (3.3 g) (see Preparation 18) in ethanol (25 ml). The mixture was stirred for a erther hour before removing the solvent under reduced pressure to give a residue. The residue was then suspended in water (50 ml), cooled to 0° C. and the mixture first acidified to pH1 with 2N aqueous hydrochloric acid solution and then basified to pH14 by addition of solid sodium carbonate before being extracted with ethyl acetate (3×200 ml). The organic phases were combined, dried over anhydrous sodium sulphate and the solvent removed under reduced pressure to yield 3-(3,4-dichlorophenyl)-4-(imidazol-1-yl)butan-1-ol (2.84 g) as a cream solid.
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