Chloromethyl ethyl ether → Diethyl 1-(ethoxymethyl)-5-methyl-3-phenyl-pyrrole-2,4-dicarboxylate

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Reaction Steps

Potassium tert-butoxide (557 mg, 4.97 mmol) was added to a stirred solution of diethyl 5-methyl-3-phenyl-1H-pyrrole-2,4-dicarboxylate (600 mg, 1.99 mmol) in dimethylsulfoxide (15 mL) at 10° C. and stirred at ambient temperature for 1 h. Upon cooling to 10° C., chloromethyl ethyl ether (377 mg, 3.99 mmol) was added and stirred at ambient temperature for 12 h. The mixture was poured onto ice-water and extracted with diethyl ether (5×10 mL). The combined organic layers were washed with water, brine, dried over anhydrous sodium sulphate and filtered. The filtrate was concentrated in vacuo and subjected to column chromatography over silica gel (100-200 mesh) using 8% ethyl acetate in petroleum ether as eluent to afford diethyl 1-(ethoxymethyl)-5-methyl-3-phenyl-pyrrole-2,4-dicarboxylate (400 mg, 56%) as a liquid.

Provenance & Evidence