反应详情

In toluene (250 ml), N,N′-dibenzylethylenediamine (12 ml) and triethylamine (12 ml) were dissolved, followed by the dropwise addition of methyl 3-bromocrotonate (7.0 ml) under ice cooling. The resulting mixture was stirred at room temperature for 24 hours. After the addition of triethylamine (2.0 ml), the resulting mixture was stirred at room temperature for 71 hours. The insoluble matter was filtered off and the filtrate was distilled under reduced pressure. The residue was added with 10% hydrochloric acid (300 ml) and crystals so precipitated were removed by filtration. Ethyl acetate was added to the filtrate. Potassium carbonate was added to the water layer so separated to make it alkaline. Ethyl acetate was added to the resulting mixture. The organic layer so separated was washed with saturated aqueous NaCl solution and dried over anhydrous potassium carbonate. The solvent was then distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column (hexane ethyl acetate=4:1), whereby the title compound (10.7 g, 62%) was obtained.

1. stirringthe resulting mixture was stirred at room temperature for 71 hours
2. filtrationThe insoluble matter was filtered off
3. distillationthe filtrate was distilled under reduced pressure
4. additionThe residue was added with 10% hydrochloric acid (300 ml) and crystals
5. customso precipitated
6. customwere removed by filtration
7. additionEthyl acetate was added to the filtrate
8. additionPotassium carbonate was added to the water layer
9. customso separated
10. additionEthyl acetate was added to the resulting mixture
11. customThe organic layer so separated
12. washwas washed with saturated aqueous NaCl solution
13. dry with materialdried over anhydrous potassium carbonate
14. distillationThe solvent was then distilled off under reduced pressure
15. customThe residue was purified by chromatography on a silica gel column (hexane ethyl acetate=4:1), whereby the title compound (10.7 g, 62%)
16. customwas obtained