Methyl Acrylate → HCID 118022928, compound

Participants

Reaction Conditions

Reaction Steps

A 500 mL, 3-neck round bottom flask was charged with methyl acrylate (18.9 g, 220 mmol) and ethanol (110 mL). 3-hydrazinopyridine dihydrochloride (20.0 g, 110 mmol) was added, followed by sodium ethoxide (29.9 g, 439 mmol) and the reaction was stirred at 60° C. for 6 hours, at which point thin layer chromatography (TLC) analysis [Eluent: 10% methanol/dichloromethane] indicated that the starting material had disappeared and a major product had formed: ESIMS m/z 164 ([M+H]+). The reaction was allowed to cool to 20° C. and concentrated to afford a yellow solid. The resulting solid was charged with phosphoryl chloride (100 g, 654 mmol). The reaction was stirred at 60° C. for 3 hours, at which point a sample of the reaction mixture was diluted with water and basified with 15 wt % sodium hydroxide (NaOH) solution. The resulting solution was extracted with ethyl acetate (EtOAc) and the organic layer was analyzed by thin layer chromatography [Eluent: ethyl acetate], which indicated that the reaction was complete.

Provenance & Evidence