Ethyl (2,5-dimethyl-1H-pyrrol-1-yl)acetate → HCID 53246737, compound

Participants

Reaction Conditions

Reaction Steps

To a 0° C. solution of ethyl 2-(2,5-dimethyl-1H-pyrrol-1-yl)acetate (0.2 g, 1.10 mmol) in dichloromethane (8.0 mL) was added diethylaluminum chloride (1.66 mL, 1.66 mmol). The reaction was stirred at 0° C. for 15 minutes, after which a solution of 2-(morpholinosulfonyl)benzoyl chloride (0.384 g, 1.32 mmol) was added. The reaction was stirred for 30 minutes at 0° C., then allowed to warm to room temperature, and stirred for 3 hours at this temp. The reaction was quenched with sodium bicarbonate (15 mL), extracted with dichloromethane (3×50 mL), washed with brine, dried (sodium sulfate), filtered, and concentrated. Purification by column chromatography on silica gel using 30 to 100% ethyl acetate in hexanes afforded ethyl 2-(2,5-dimethyl-3-(2-(morpholinosulfonyl)benzoyl)-1H-pyrrol-1-yl)acetate (0.145 g, 0.334 mmol, 30% yield). 1H NMR (400 MHz, CDCl3): δ (ppm) 7.84 (d, 1H), 7.61 (app. t, 1H), 7.55 (dd, 1H), 7.39 (d, 1H), 5.72 (s, 1H), 4.51 (s, 2H), 4.23 (q, 2H), 3.68-3.71 (m, 4H), 3.14-3.17 (m, 4H), 2.44 (s, 3H), 2.07 (s, 3H), 1.29 (t, 3H).

Provenance & Evidence