Sodium borohydride → 2-(4-(Hydroxymethyl)-1H-indol-1-yl)benzonitrile

反応式

[BH4-].[Na+].[CH:3]([C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][N:9]2[C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[C:16]#[N:17])=[O:4]>CCO.C(Cl)Cl>[OH:4][CH2:3][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][N:9]2[C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[C:16]#[N:17]

参加物

実験手順

NaBH4 (50 mg, 1.35 mmol Eq: 0.4) was added to a solution of 2-(4-formyl-1H-indol-1-yl)benzonitrile (810 mg, 3.29 mmol, Eq: 1.00) in EtOH (30 mL) and DCM (15 mL) at 0° C. and the mixture warmed to RT. After 3 h., the mixture was concentrated to remove the DCM. The resulting mixture was diluted with sat. NH4Cl, extracted with DCM and the combined extracts concentrated. The residue was purified by silica gel chromatography to afford the title compound (810 mg, 99%) as a white solid.