反应详情

3,4,5-Triethoxybenzoic acid (2.54 g) was dissolved in tetrahydrofuran (250 ml), and lithium aluminum hydride (1.20 g) was added thereto, followed by heating under reflux for 24 hours. Ethyl acetate and then a 2N aqueous solution of sodium hydroxide were added to the reaction solution, insoluble matters were filtered off, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (100 ml), and manganese dioxide (5.10 g) was added thereto, followed by stirring for 120 hours. Insoluble matters were filtered off, and the filtrate was concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (100 ml), and ethylmagnesium bromide (1M tetrahydrofuran solution, 15 ml) was added thereto, followed by stirring at room temperature for 30 minutes. 1N Hydrochloric acid was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in acetone (100 ml), and Jones' reagent (2 ml) was added thereto under ice-cooling, followed by stirring at the same temperature for 30 minutes. 2-Propanol (10 ml) was added to the reaction solution and the mixture was concentrated under reduced pressure. The residue was subjected to partitioning between ethyl acetate and water. The organic layer was washed with a saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 3',4',5'-triethoxypropiophenone (0.76 g).

1. temperatureby heating
2. temperatureunder reflux for 24 hours
3. filtrationwere filtered off
4. concentrationthe filtrate was concentrated under reduced pressure
5. dissolutionThe residue was dissolved in ethyl acetate (100 ml)
6. additionmanganese dioxide (5.10 g) was added
7. filtrationInsoluble matters were filtered off
8. concentrationthe filtrate was concentrated under reduced pressure
9. dissolutionThe residue was dissolved in tetrahydrofuran (100 ml)
10. additionethylmagnesium bromide (1M tetrahydrofuran solution, 15 ml) was added
11. stirringby stirring at room temperature for 30 minutes
12. addition1N Hydrochloric acid was added to the reaction solution
13. extractionthe mixture was extracted with ethyl acetate
14. washThe organic layer was washed with a saturated saline
15. dry with materialdried over anhydrous magnesium sulfate
16. concentrationconcentrated under reduced pressure
17. dissolutionThe residue was dissolved in acetone (100 ml)
18. additionJones' reagent (2 ml) was added
19. temperatureunder ice-cooling
20. stirringby stirring at the same temperature for 30 minutes
21. addition2-Propanol (10 ml) was added to the reaction solution
22. concentrationthe mixture was concentrated under reduced pressure
23. customto partitioning between ethyl acetate and water
24. washThe organic layer was washed with a saturated saline
25. dry with materialdried over anhydrous magnesium sulfate
26. concentrationconcentrated under reduced pressure
27. customThe residue was purified by silica gel column chromatography