Hydrochloric Acid → 3(S)-(3,4-dichlorophenyl)-4-(imidazol-1-yl)butan-1-ol

Participants

Reaction Steps

Sodium borohydride (0.68 g) was added carefully to an ice-cooled solution of 3(S)-(3,4-dichlorophenyl)-4-(imidazol-1-yl)butan-1-al (4.3 g) (see Preparation 97) in ethanol (40 ml) and the mixture stirred at room temperature for one hour before removing the solvent under reduced pressure to give a residue. The residue was suspended in water (30 ml), cooled in an ice-bath and the mixture first acidified to pH1 with 2N aqueous hydrochloric acid solution and then basified to pH14 by addition of 2N aqueous sodium hydroxide solution. The resulting suspension was filtered and the residue washed with water, dried and then crystallised from acetonitrile to give 3(S)-(3,4-dichlorophenyl)-4-(imidazol-1-yl)butan-1-ol (1.37 g) as a cream solid.

Provenance & Evidence