反应详情

Compound 31B (3.7 g, 13.39 mmol) was dissolved in 1,4-dioxane (30 mL) and water (5 mL). To this solution was added to sodium bicarbonate (9.0 g, 107 mmol) portionwise to control the gas formation. To the resulting suspension was added dimethyl sulfate (8.96 mL, 94 mmol). The reaction was heated under reflux for 2 hours. The reaction mixture was concentrated, and partitioned between water and EtOAc. The aqueous layer was extracted with additional EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with 7:3/hexanes: EtOAc to provide 3.1 g of the desired product: 1H NMR (DMSO-d6): δ 7.64-7.68 (m, 2H), 7.34-7.69 (m, 5H), 7.22-7.26 (m, 2H), 5.22 (s, 2H), 3.92 (s, 3H). MS (DCI(+)): m/z 308 (M+NH4).

1. temperatureThe reaction was heated
2. temperatureunder reflux for 2 hours
3. concentrationThe reaction mixture was concentrated
4. custompartitioned between water and EtOAc
5. extractionThe aqueous layer was extracted with additional EtOAc
6. washThe combined organic layers were washed with brine
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by flash column chromatography on silica gel eluting with 7:3/hexanes