Methyl 3-(1-methylindol-3-YL)propanoate → 3-(1-Methyl-1H-indol-3-yl)propan-1-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-(1-methyl-3-indolyl)propionate (300 mg, 1.38 mmol) in Et2O (3.0 mL) was added LiAlH4 at 0° C. under N2 atmosphere. The reaction mixture was stirred for 30 min at 0° C. and quenched by careful addition of H2O. EtOAc was added to the quenched reaction mixture. The organic layer was separated, washed with brine and dried over MgSO4. It was then concentrated in vacuo and chromatographed on a silica gel column by elution with EtOAc/Hexanes to give 3-(1-methyl-3-indolyl)-1-propanol (250 mg, 96%) as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ1.28 (t, 1H, J=6.2 Hz), 1.98 (qu, 2H, J=7.7 Hz), 2.85 (t, 2H, J=7.3 Hz), 3.70-3.78 (m, 4H), 6.86 (s, 1H), 7.10 (dt, 1H, J=1.1, 7.0 Hz), 7.22 (dt, 1H, J=1.1, 7.5 Hz), 7.29 (d, 1H, J=8.1 Hz), 7.60 (d, 1H, J=7.7 Hz) ppm.

Provenance & Evidence