反应详情

温度

80 °C

75.09 g of methyl isobutyrylacetate (0.50 mol, concentration 96%) and 61.8 g of 4-fluorobenzonitrile (0.50 mol, concentration 98%) were dissolved in 500 ml of toluene and treated with 144.72 g of tin tetrachloride (0.55 mol, concentration 99%) at room temperature over the course of 15 min. After half an hour at room temperature, the mixture was heated to 80° C. After 3 h, the suspension was cooled to 10° C. and treated with 500 ml of water. The mixture was diluted with 100 ml of dichloroethane and the phases were separated. The organic phase was washed with 2×100 ml of 1N sodium hydroxide solution. After concentration in vacuo, 125.5 g of crude product were obtained in the form of a yellowish solid. The solid was dissolved in 160 ml of n-hexane under reflux and filtered hot. The product precipitated from the filtrate on cooling. By filtering through a frit and washing the filter cake with 130 ml of n-hexane, 79.8 g of methyl 2-[1-amino-1-(4-fluorophenyl)methylene]-4-methyl-3-oxopentanoate were obtained in the form of a spectroscopically pure solid.

1. waitAfter half an hour at room temperature
2. temperaturethe suspension was cooled to 10° C.
3. customthe phases were separated
4. washThe organic phase was washed with 2×100 ml of 1N sodium hydroxide solution
5. concentrationAfter concentration in vacuo
6. custom125.5 g of crude product were obtained in the form of a yellowish solid
7. temperatureunder reflux
8. filtrationfiltered hot
9. customThe product precipitated from the filtrate
10. temperatureon cooling
11. filtrationBy filtering through a frit
12. washwashing the filter cake with 130 ml of n-hexane