反应详情

ADDP (49.0 g, 194.09 mmol) was added to a mixture of 2-(6-methoxypyridin-2-yl)ethanol (22.87 g, 149.30 mmol), phthalimide (24.16 g, 164.23 mmol), tributylphosphine (48.5 mL, 194.09 mmol) and THF (340 mL) at 0° C. under argon atmosphere to give a solution. The solution was stirred at room temperature for 16 hr, to the reaction mixture was added ethyl acetate (about 500 mL), and the mixture was stirred at 0° C. for 20 min. The insoluble substance was removed by filtration with ethyl acetate, and washed with ethyl acetate. The filtrate was poured into water (1000 mL), and the mixture was extracted with ethyl acetate (×3). The organic layer was washed with water and brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 5→20% ethyl acetate/hexane), and the precipitate was collected by filtration with hexane to give 2-(2-(6-methoxypyridin-2-yl)ethyl)isoindoline-1,3-dione (29.03 g, 103 mmol, 69%) as an off-white powder.

1. customto give a solution
2. stirringthe mixture was stirred at 0° C. for 20 min
3. customThe insoluble substance was removed by filtration with ethyl acetate
4. washwashed with ethyl acetate
5. additionThe filtrate was poured into water (1000 mL)
6. extractionthe mixture was extracted with ethyl acetate (×3)
7. washThe organic layer was washed with water and brine
8. dry with materialdried over magnesium sulfate
9. customthe solvent was evaporated under reduced pressure
10. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 5→20% ethyl acetate/hexane)
11. filtrationthe precipitate was collected by filtration with hexane