Dimethylformamide → HCID 66914857, compound

Participants

Reaction Steps

Sodium hydride (55%; 555 mg, 12.7 mmol) was added to a solution of 2-ethyl 4-methyl 3-isopropyl-5-methyl-1H-pyrrole-2,4-dicarboxylate (1.8 g, 6.74 mmol) in dry dimethylformamide (10 mL) at 0-5° C. and stirred for 30 min. 1-Bromo-2-methoxy-ethane (1.0 mL, 10.1 mmol) was added dropwise to the mixture which was stirred at 90° C. for 2 h. Additional sodium hydride (55%; 275 mg, 6.37 mmol) was added followed by 1-bromo-2-methoxy-ethane (1.0 mL, 10.1 mmol) and stirring continued at 90° C. for 5 h. The reaction mixture was cooled to room temperature, quenched with ice water and extracted with ethyl acetate (2×30 mL). The combined organic phases were washed with water (2×50 mL), brine (50 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford diethyl 3-isopropyl-1-(2-methoxyethyl)-5-methyl-pyrrole-2,4-dicarboxylate (2.2 g, 100%).

Provenance & Evidence