Methyl formate → Methyl 3-hydroxy-2-(1-methylpyrrol-2-yl)propenoate

Participants

Reaction Steps

Sodium hydride (3.05 g, 50% dispersion in oil, 64 mmol) was washed with 40°-60° C. petroleum ether and then suspended in dry DMF (30 ml) under an atmosphere of nitrogen. A solution of methyl (1-methylpyrrol-2-yl)acetate (5 g, 32 mmol) and methyl formate (39.5 ml, 64 mmol) in DMF (10 ml) was then added dropwise at room temperature with vigorous stirring. After 3 hours, the reaction mixture was poured into 10% aqueous potassium carbonate (100 ml) and extracted with ether (2 × 100 ml). The aqueous layer was treated with concentrated hydrochloric acid and re-extracted with ether (2 ×100 ml). The combined ether layers were dried and evaporated to give methyl 3-hydroxy-2-(1-methylpyrrol-2-yl)propenoate (5.4 g) as an orange oil which was used without further purification.

Provenance & Evidence