Ethanol → 2-Ethenylquinoxaline

Participants

Reaction Steps

Dimethyl sulfate (1.07 ml, 11.3 mmol) was added dropwise, while maintaining the mixture temperature below 40° C., to a solution of amine (a) (2.6 g 11.3 mmol) in ethanol (3 ml). The thick mixture was diluted with water (15 ml) then triethylamine (1.13 ml) was added and the mixture heated for 2 hours on a water bath. After cooling the mixture was extracted with diethyl ether. The organic phase was dried over magnesium sulfate, concentrated to dryness and the residue was chromatographed on silica eluting with heptane-ethyl acetate (3-1) to give the product (1.16 g, 66%).

Provenance & Evidence