Methyl propiolate → HCID 178492908, compound

Participants

Reaction Conditions

Reaction Steps

2-Fluoro-4-methoxyphenylamine (3.80 g, 26.7 mmole) and methyl propiolate (2.37 ml, 0.267 mole) in methanol (100 ml) was stirred for 72 hours at room temperature, then heated at 50° C. for 24 hours. It was evaporated and the product purified by chromatography on silica gel (dichloromethane) to give a solid (1.66 g), a portion of which was recrystallised from dichloromethane-hexane. The unsaturated ester (0.96 g) in warm Dowtherm A (5 ml) was added over 3 minutes to refluxing Dowtherm A (15 ml), and after a further 20 minutes at reflux the mixture was cooled and poured into diethyl ether. The precipitate was filtered to give the title compound (0.50 g, 61%). MS (ES) m/e 196 (M+H)+.

Provenance & Evidence