反应详情

To a mixture of 1-(2-hydroxyphenyl)propan-1-one (10.0 g), methyl bromoacetate (5.11 mL) and acetone (100 mL) was added potassium carbonate (18.4 g), and the mixture was stirred overnight at room temperature. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio) to give a colorless oil. To a solution (150 mL) of the obtained oil in N,N-dimethylformamide was added 1,8-diazabicyclo[5.4.0]undec-7-ene (8.12 mL), and the mixture was stirred at 120° C. for 2 hr. 1N Hydrochloric acid was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. Ethyl acetate was added to the residue, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9, volume ratio) to give the title object compound (7.14 g, 52%) as a white solid.

1. filtrationThe insoluble material was filtered off
2. concentrationthe filtrate was concentrated under reduced pressure
3. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio)
4. customto give a colorless oil
5. stirringthe mixture was stirred at 120° C. for 2 hr
6. customto quench
7. customthe reaction
8. extractionthe mixture was extracted with ethyl acetate
9. washThe extract was washed with saturated brine
10. dry with materialdried over magnesium sulfate
11. concentrationconcentrated under reduced pressure
12. additionEthyl acetate was added to the residue
13. filtrationthe insoluble material was filtered off
14. concentrationthe filtrate was concentrated under reduced pressure
15. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9, volume ratio)