Hydrochloric Acid → 6-Methoxy-1-(phenylsulfonyl)-1H-indole-4-carbaldehyde

Participants

Reaction Steps

6-Methoxy-1-(phenylsulfonyl)-4-vinyl-1H-indole (0.27 g, 0.9 mmol; Intermediate 33) was dissolved in dioxane (24 mL) and 2,6-lutidine (0.2 mL, 1.7 mmol) was added. Osmium tetraoxide (0.011 g, 0.04 mmol) was added and after 15 min of stirring did the mixture change colour to black. Sodium periodate (0.74 g, 3.4 mmol) dissolved in water (8 mL, warmed to dissolve) was added and a precipitation started to form. After 1 h of stirring at rt was the mixture portioned between 2N HCl and dichloromethane. The organic layer was dried (Na2SO4) and concentrated to give 0.41 g of the crude product. MS (ESI+) for C16H13NO4S m/z 316 (M+H)+.

Provenance & Evidence