反应详情

p-Tolyl magnesium bromide (1 M solution in diethyl ether, 4.2 mL, 4.17 mmol) was added slowly to a solution of 6-bromo-4,4-dimethyl-3,4-dihydro-2H-naphthalen-1-one (Compound 3, 350 mg, 1.39 mmol) in 10 mL of diethyl ether at 0° C. After stirring and warming to room temperature for 2 h, the mixture was quenched with water at 0° C., extracted with diethyl ether (3×5 mL), washed with brine (1×5 mL), dried (MgSO4) and concentrated at reduced pressure to give a light yellow oil. The crude oil was then dissolved in 10 mL of dichloromethane and stirred with 100 mg of para-toluenesulfonic acid at room temperature for 2 h. Water (10 mL) was then added and the organic layer was washed with brine (1×5 mL), dried (MgSO4) and concentrated at reduced pressure. Purification by flash chromatography (hexane) gave the title compound (295 mg, 65% yield) as a colorless oil:

1. customthe mixture was quenched with water at 0° C.
2. extractionextracted with diethyl ether (3×5 mL)
3. washwashed with brine (1×5 mL)
4. dry with materialdried (MgSO4)
5. concentrationconcentrated at reduced pressure
6. customto give a light yellow oil
7. washthe organic layer was washed with brine (1×5 mL)
8. dry with materialdried (MgSO4)
9. concentrationconcentrated at reduced pressure
10. customPurification by flash chromatography (hexane)