p-Toluenesulfonic acid monohydrate → (5-Chloro-7-methyl-1-tosyl-1H-indol-4-yl)methanol

Participants

Reaction Steps

A solution of (±)-5-chloro-7-methyl-4-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-1-tosyl-1H-indole (4.1 g, 9.5 mmol) and TsOH.H2O (359 mg, 1.9 mmol) in EtOH (50 mL) was stirred at room temperature for 21 h. The reaction mixture was concentrated. The mixture was diluted with CH2Cl2. The organic phase was successively washed with 5% aq. NaHCO3, H2O and brine, dried over Na2SO4, and then filtered. Concentration of the filtrate gave the title compound, without need of further purification. 1H NMR (400 MHz, ACETONITRILE-d3) δ 7.84 (d, J=3.79 Hz, 1H), 7.59 (d, J=8.34 Hz, 2H), 7.33 (d, J=8.34 Hz, 2H), 7.10 (s, 1H), 7.00 (d, J=3.79 Hz, 1H), 4.84 (d, J=5.81 Hz, 2H), 3.14 (t, J=5.81 Hz, 1H), 2.52 (s, 3H), 2.37 (s, 3H).

Provenance & Evidence