Potassium Carbonate → HCID 20464780, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred, refluxing mixture of ethyl glycinate hydrochloride (100 g, 0.71 m), ethyl 2,4-dioxo-5-(3-methylphenoxy)pentanoate (187 g, 0.71 m) and benzene (650 ml) under a nitrogen atmosphere is added finely powdered anhydrous potassium carbonate (50 g, 0.36 m) in five portions over one hour, the eliminated water being collected in a Dean-Stark trap until the theoretical amount (12.6 ml) is collected. The mixture is cooled to 5° C., then 750 ml dry ethanol is added and sodium metal (16.5 g, 0.71 mol) is added in small pieces at a rate which permits the internal reaction temperature to be maintained at less than 40° with cooling. Stirring is continued in the ice bath for an additional 1/2 hour, and the reaction mixture is then poured into a 5-liter separatory funnel containing ether (1 liter) and water (2 liters). The layers are separated and the aqueous layer is re-extracted with ether. The combined ether layers are washed with water and saturated brine. The organic layer is dried over sodium sulfate and concentrated to give a residue which is purified by preparative HPLC to afford diethyl 4-(3-methylphenoxy)methylpyrrole-2,5-dicarboxylate.

Provenance & Evidence