Acetone → 2-(Hydroxymethyl)-5-methoxy-1-methyl-1H-indole-4,7-dione

Participants

Reaction Steps

A solution of potassium nitrosodisulfonate (KSO3)2NO (590 mg, 2.2 mmol) in sodium phosphate buffer (0.4 M, pH=6, 13 mL) was added to a solution of 11 (130 mg, 0.63 mmol) in acetone (8 mL). The reaction mixture was stirred for 1 h at room temperature, ethyl acetate and water were added, and the aqueous layer was extracted (EtOAc, 3×). The combined organic layers were dried over Na2SO4 and evaporated. Column chromatography of the crude product (EtOAc) afforded 12 (122 mg, 87%) as an orange solid; Rf=0.62 (EtOAc); 1H NMR (CDCl3): δ 6.58 (1H, s), 5.67 (1H, s), 4.68 (2H, s), 4.03 (3H, s), 3.83 (3H, s).

Provenance & Evidence