o-Toluenesulfonyl chloride → 1-{1-[(4-Methylphenyl)sulfonyl]-1H-indol-3-yl}ethanone

Participants

Reaction Steps

Add 1.0 M t-BuOK (3.0 mL, 0.003 mol) to a stirring solution of 3-acetyl indole (0.478 g, 0.0030 mol) in dry DMF (20 mL) under N2 at ambient temperature and stir for 30 min. Add toluenesulfonyl chloride to this solution and stir the resulting mixture overnight. Pour the reaction into EtOAc—H2O, separate the organic layer and extract several times with H2O wash with brine, dry (MgSO4), filter, and evaporate on the rotary evaporator. Chromatograph on the ISCO eluting with a gradient hexane-EtOAc (0-100%) over 30 minutes to give 0.73 g (78%) of the title compound as a solid: 1H (CDCl3). δ 7.8 (d, 1H), 8.2 (s, 1H), 7.9 (d, 1H), 7.7 (d, 2H), 7.4 (m, 2H), 7.3 (d, 2H), 2.6 (s, 3H), 2.4 (s, 3H).

Provenance & Evidence