反应详情

3-Methoxy-4,5-methylenedioxybenzaldehyde (5.55 g) was dissolved in tetrahydrofuran (150 ml), and ethylmagnesium bromide (IM tetrahydrofuran solution, 46.2 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 successively with water, a 5% aqueous solution of sodium bicarbonate and a saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in acetone (300 ml), and Jones' reagent (5.3 ml) was added thereto under ice-cooling, followed by stirring at the same temperature for 30 minutes. 2-Propanol (5.3 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 successively with water and 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'-methoxy-4',5'-methylenedioxypropiophenone (5.27 g).

1. extractionthe mixture was extracted with ethyl acetate
2. washThe organic layer was washed successively with water
3. dry with materiala 5% aqueous solution of sodium bicarbonate and a saturated saline, dried over anhydrous magnesium sulfate
4. concentrationconcentrated under reduced pressure
5. dissolutionThe residue was dissolved in acetone (300 ml)
6. additionJones' reagent (5.3 ml) was added
7. temperatureunder ice-cooling
8. stirringby stirring at the same temperature for 30 minutes
9. addition2-Propanol (5.3 ml) was added to the reaction solution
10. concentrationthe mixture was concentrated under reduced pressure
11. customto partitioning between ethyl acetate and water
12. washThe organic layer was washed successively with water
13. dry with materiala saturated saline, dried over anhydrous magnesium sulfate
14. concentrationconcentrated under reduced pressure
15. customThe residue was purified by silica gel column chromatography