反应详情

445 mg of 3′-allyl-2′-hydroxy-4′-methoxyacetophenone and 0.57 g of methoxyacetone were dissolved in 10 ml of toluene. Thereafter, 0.19 g of pyrrolidine and 0.19 ml of acetic acid were added to the reaction solution. Thereafter, the reaction solution was heated to reflux using Dean-Stark for 1 hour. Thereafter, the reaction solution was cooled to a room temperature. 1.14 g of methoxyacetone, 0.38 g of pyrrolidine, and 0.38 ml of acetic acid were added to the reaction solution, and the obtained mixture was further heated to reflux overnight. The reaction solution was cooled to a room temperature and then concentrated under a reduced pressure. The residue was diluted with ethyl acetate, and then successively washed with 2 N hydrochloric acid, a 1 N sodium hydroxide aqueous solution, water, and a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate), so as to obtain 194 mg of the subject compound.

1. temperatureThereafter, the reaction solution was heated
2. temperatureto reflux
3. customfor 1 hour
4. temperaturethe obtained mixture was further heated
5. temperatureto reflux overnight
6. temperatureThe reaction solution was cooled to a room temperature
7. concentrationconcentrated under a reduced pressure
8. additionThe residue was diluted with ethyl acetate
9. washsuccessively washed with 2 N hydrochloric acid
10. dry with materialThe organic layer was dried over magnesium sulfate
11. concentrationconcentrated under a reduced pressure
12. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)