反应详情

To a solution of 6-bromo-4-phenyl-3-isocoumarincarboxylic acid methyl ester (359 mg) in methanol (20 ml) was added 3-(4-aminomethylphenyl)propionic acid methyl ester (387 mg) and the mixture was stirred at room temperature for 18 hr. The solvent was evaporated under reduced pressure, 1N hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried by adding sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was dissolved in methanol (30 ml) and conc. sulfuric acid (3 ml) was added. The mixture was heated under reflux for 3 hrs. The solvent was evaporated under reduced pressure, water was added under ice-cooling and the mixture was neutralized with potassium carbonate. The solution was extracted with ethyl acetate. The extract was washed with saturated brine and dried by adding sodium sulfate. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=19/1→3/1) to give the title compound (425 mg, 80%).

1. customThe solvent was evaporated under reduced pressure, 1N hydrochloric acid
2. additionwas added
3. extractionthe mixture was extracted with ethyl acetate
4. washThe extract was washed with saturated brine
5. customdried
6. additionby adding sodium sulfate
7. customThe solvent was evaporated under reduced pressure
8. dissolutionthe obtained residue was dissolved in methanol (30 ml)
9. additionconc. sulfuric acid (3 ml) was added
10. temperatureThe mixture was heated
11. temperatureunder reflux for 3 hrs
12. customThe solvent was evaporated under reduced pressure, water
13. additionwas added under ice-
14. temperaturecooling
15. extractionThe solution was extracted with ethyl acetate
16. washThe extract was washed with saturated brine
17. customdried
18. additionby adding sodium sulfate
19. customThe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=19/1→3/1)