Dichloromethane → (2-tert-butyl-5-nitro-1H-indol-7-yl)methanol

반응식

[C:1]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:8]=2[C:17](OC)=[O:18])([CH3:4])([CH3:3])[CH3:2].ClCCl.CC(C[AlH]CC(C)C)C>O>[C:1]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:8]=2[CH2:17][OH:18])([CH3:4])([CH3:2])[CH3:3]

참가 물질

실험 절차

To a solution of methyl 2-tert-butyl-5-nitro-1H-indole-7-carboxylate (6.15 g, 22.3 mmol) and dichloromethane (30 ml) was added DIBAL-H (1.0 M, 20 mL, 20 mmol) at 78° C. The mixture was stirred for 1 h before water (10 mL) was added slowly. The resulting mixture was extracted with EtOAc (120 mL×3). The combined organic extracts were dried over anhydrous Na2SO4 and evaporated under vacuum to give (2-tert-butyl-5-nitro-1H-indol-7-yl)methanol (4.0 g, 73%), which was used in the next step directly.