Hydrochloric Acid → 3-Phenyl-1-(toluene-4-sulfonyl)-1H-indole-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of oxalyl chloride (1.37 g, 10.8 mmol) in DCM (30 mL) at −78° C. and under a nitrogen atmosphere was added DMSO (1.50 mL, 21.6 mmol). After stirring for 10 min at −78° C., a solution of [3-phenyl-1-(toluene-4-sulfonyl)-1H-indol-2-yl]methanol (2.27 g, 6.01 mmol) in DCM (20 mL) was added and stirring was continued for 1.5 h. Triethylamine was added and, after stirring for 10 min at −78° C., the mixture was slowly warmed to RT. The reaction mixture was poured into a 1.0M aq HCl solution and extracted with DCM (×3). The combined organic layers were washed with water, then brine, dried (Na2SO4) and concentrated in vacuo affording the title compound as a gum which then solidified on standing to give an off-white solid (2.26 g, 100%). 1H NMR (CDCl3, 400 MHz): δ 10.22 (1H, s), 8.31 (1H, d, J=8.56 Hz), 7.86-7.81 (2H, m), 7.60-7.41 (7H, m), 7.33-7.21 (3H, m), 2.37 (3H, s)

Provenance & Evidence