Dimethylformamide → Diethyl 5-ethyl-1-(methoxymethyl)-3-phenyl-pyrrole-2,4-dicarboxylate

Participants

Reaction Steps

Sodium hydride (50% in mineral oil; 220 mg, 4.76 mmol) was added to a solution of diethyl 5-methyl-3-phenyl-1H-pyrrole-2,4-dicarboxylate (1 g, 3.18 mmol) in dimethylformamide (15 mL) at 0° C. and then the mixture stirred for 30 min at ambient temperature. The mixture was cooled to 0° C. and chloro-methoxy-methane (0.3 ml, 3.8 mmol) was added and the whole refluxed for 6 h. The reaction mixture was cooled, washed with water (2×25 ml) and extracted with ethyl acetate (4×25 ml). The combined ethyl acetate extracts were washed with water (2×25 ml), brine (25 ml), dried over anhydrous sodium sulphate and concentrated to afford diethyl 5-ethyl-1-(methoxymethyl)-3-phenyl-pyrrole-2,4-dicarboxylate (1 g, 88%) as a pale yellow liquid.

Provenance & Evidence