反应详情

温度

-30 °C

50% Sodium hydride (4.8 g, 0.1 mol) was washed with petroleum ether and then suspended under nitrogen in dry tetrahydrofuran (50 ml) at -30° C. Ethyl 3-(2-methoxyphenylamino)acrylate (17.4 g, 0.1 mol) in dry tetrahydrofuran (100 ml) was added dropwise to the stirred suspension keeping the temperature below -20° C. Cooling was removed and the mixture was stirred until a deep red colour was obtained. The mixture was re-cooled to -30° C. and hexanoyl chloride (13.8 ml, 0.1 mol) in dry tetrahydrofuran (50 ml) was added dropwise. Cooling was again removed and the mixture was stirred for 2 hours. The mixture was partitioned between 10% hydrochloric acid and dichloromethane then washed with water and brine, dried and evaporated to afford an oil which was chromatographed (silica gel, chloroform) to give ethyl 2-hexanoyl-3-(2-methoxyphenyl- amino)acrylate, (20 g, 62.7%).

1. customthe temperature below -20° C
2. temperatureCooling
3. customwas removed
4. customwas obtained
5. temperatureCooling
6. customwas again removed
7. stirringthe mixture was stirred for 2 hours
8. customThe mixture was partitioned between 10% hydrochloric acid and dichloromethane
9. washthen washed with water and brine
10. customdried
11. customevaporated
12. customto afford an oil which
13. customwas chromatographed (silica gel, chloroform)