反应详情

A stirred solution of ethyl 2-cyano-2-(formylamino)acetate (J. Org. Chem., 1979, 44, 3835; 0.47 g, 0.003 mol), acrylonitrile (1.2 ml, 0.018 mol) and tri-fluoroacetic acid (0.02 ml, 0.0003 mol) in 1,2-dichloroethane (4 ml) was heated under reflux for 3 days. The solvent was removed by evaporation under vacuum, the residue dissolved in dichloromethane (30 ml) and the resulting solution washed with saturated aqueous sodium bicarbonate solution (30 ml). The aqueous phase was washed with dichloromethane (30 ml) and the organic solutions then combined, dried (MgSO4) and evaporated under vacuum. Chromatography of the residue on silica gel (12 g), eluting with dichloromethane:methanol (100:1), followed by crystallization from acetone:hexane, gave the title compound as a colourless solid (0.12 g, 21%), m.p. 114-116° C.

1. temperatureunder reflux for 3 days
2. customThe solvent was removed by evaporation under vacuum
3. dissolutionthe residue dissolved in dichloromethane (30 ml)
4. washthe resulting solution washed with saturated aqueous sodium bicarbonate solution (30 ml)
5. washThe aqueous phase was washed with dichloromethane (30 ml)
6. dry with materialdried (MgSO4)
7. customevaporated under vacuum
8. washChromatography of the residue on silica gel (12 g), eluting with dichloromethane:methanol (100:1)
9. customfollowed by crystallization from acetone