反应详情

[Step 2] To a solution of 3-acetyl-6-bromo-4-phenyl-isochromen-1-one (1.03 g) in methanol (100 ml) were added 4-aminomethyl-benzoic acid methyl ester hydrochloride (3.02 g) and triethylamine (4.2 ml) and the mixture was stirred at room temperature for 18 hrs. 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, 4N hydrochloric acid ethyl acetate solution (5 ml) was added to the obtained residue, and the mixture was stirred at room temperature for 10 hrs. The solvent was evaporated under reduced pressure, water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated sodium hydrogen carbonate solution and 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 (220 mg, 15%).

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, 4N hydrochloric acid ethyl acetate solution (5 ml)
8. additionwas added to the obtained residue
9. stirringthe mixture was stirred at room temperature for 10 hrs
10. customThe solvent was evaporated under reduced pressure, water
11. additionwas added
12. extractionthe mixture was extracted with ethyl acetate
13. washThe extract was washed with saturated sodium hydrogen carbonate solution and saturated brine
14. customdried
15. additionby adding sodium sulfate
16. customThe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=19/1→3/1)