Water → 4-Chloro-5-[(methyloxy)carbonyl]-1H-pyrrole-2-carboxylic acid

Participants

Reaction Steps

KMnO4 (2.53 g, 16.0 mmol) was dissolved in acetone and water and added dropwise over a 2 hr period to a solution of methyl 3-chloro-5-formyl-1H-pyrrole-2-carboxylate (1.50 g, 8.00 mmol) in acetone (250 mL). After stirring for 4 hr the solution was poured into a solution of NaHSO3 in 1N HCl. This was extracted with EtOAc and the organic layer was washed with water. The organic layer was dried over MgSO4 and evaporated to afford the title compound (1.33 g, 82%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.15 (br. s., 1H), 12.75 (br. s., 1H), 6.78 (d, 1H), 3.77 (s, 3 H). LCMS: m/z 203.9 (M+1).

Provenance & Evidence