Methyl formate → HCID 70131010, compound

Participants

Reaction Steps

Sodium hydride (0.58 g, 50% in oil, 12 mmol) was washed with petrol (60°-80° C.) and suspended in DMF (20 ml). To this, with vigorous stirring, was added dropwise, a solution of the crude methyl(6-ethoxyindol-1-yl)acetate (1.4 g, 6 mmol) and methyl formate (1.8 ml, 30 mmol) in DMF (10 ml) at room temperature. After 3 hours the reaction mixture was poured into 10% aqueous potassium carbonate (100 ml), washed with ether (2×100 ml), neutralised with concentrated hydrochloric acid and extracted with ether (2×100 ml). These extracts were washed with brine, dried and concentrated to give methyl 3-hydroxy-2-(6-ethoxyindol-1-yl)acrylate (1.0 g, 63% yield) as an orange oil.

Provenance & Evidence