Diethyl Ether → HCID 13179851, compound

Participants

Reaction Steps

The diethyl 3-methylpyrrole-2,5-dicarboxylate obtained in Step A was taken up in dried N,N-dimethylformamide (100 ml) and added dropwise over 10 minutes, under nitrogen to an ice-cooled suspension of washed (hexane) sodium hydride (from 16.2 g, 0.41 m of 60% sodium hydride in mineral oil dispersion) in dried N,N-dimethylformamide (400 ml). The resulting mixture was then stirred without cooling for 1 hour, recooled in an ice-bath and treated dropwise over ca. 15 minutes with methyl iodide (30.3 ml, 0.49 m). After stirring for an additional 30 minutes, the mixture was slowly poured into a separatory funnel containing ether (0.5 liter) and water (1 liter). The separated ether layer was washed with water and saturated sodium chloride solution, dried, and concentrated to a tan solid. Purification via chromatography (silica gel/hexane-EtOAc) yielded diethyl 1,3-dimethylpyrrole-2,5-dicarboxylate (75 g) as a white solid, m.p. 48°-48.5° C.

Provenance & Evidence