[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:20]=[CH:19][C:18]([CH:21]=[O:22])=[CH:17][C:15]=4[CH:16]=3)=[N:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+].Cl.C(=O)([O-])O.[Na+]>CO.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][C:15]=4[CH:16]=3)=[N:9]2)=[CH:4][CH:3]=1To a cooled solution of 7-chloro-2-(5-formylbenzofuran-2-yl)quinoline (0.92 g) in a mixture of methanol (20 ml) and chloroform (10 ml) was added sodium borohydride (0.40 g) in small portions. After being stirred at the same temperature for 2 hours, the resulting mixture was treated with diluted hydrochloric acid and adjusted to be basic with aqueous sodium hydrogen carbonate. The resulting precipitates were collected by filtration, Washed with water and dried to give 7-chloro-2-(5-hydroxymethylbenzofuran-2-yl)quinoline (0.81 g).
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