Dimethylformamide → Ethyl 5-formyl-4-methyl-1H-pyrrole-2-carboxylate

Participants

Reaction Steps

To ice-cold 3 mL (39.2 mmol) of N,N-dimethylformamide (DMF) was added phosphorus oxychloride (0.67 mL, 7.18 mmol) dropwise and the resultant mixture was stirred for 30 minutes. A solution of 1 g (6.53 mmol) of 4-methyl-1H-pyrrole-2-carboxylic acid ethyl ester in 3 mL of DMF was added to the reaction. After 1 hour, the reaction was warmed to room temperature for another 2.5 hours. The reaction mixture was diluted with water (100 mL) and basified to pH=11 with 1N sodium hydroxide solution. The precipitate was removed by filtration, rinsing with water and dried to afford 0.8 g (68%) of 5-formyl-4-methyl-1H-pyrrole-2-carboxylic acid ethyl ester as a white solid. 1H NMR (360 MHz, DMSO-d6) d 12.6 (br s, 1H, NH), 9.78 (s, 1H, CHO), 6.68 (s, 1H), 4.26 (q, J=7.0 Hz, 2H, OCH2CH3), 2.28 (s, 3H, CH3), 1.28 (t, J=7.0 Hz, 3H, OCH2CH3). MS 181 [M+].

Provenance & Evidence