反应详情

温度

0 °C

A solution of 2-bromo-6-(4-tert-butyl-cyclohexyloxy)-naphthalene (2 g, 5.5 mmol) in ether (10 mL) under nitrogen was added 1.6 M n-butyllithium in hexane (4 mL, 6.4 mmol) at 0° C. The solution was stirred for 30 min at 0° C., then treated with copper(I) bromide-dimethyl sulfide complex (0.8 g, 3.9 mmol). After 2 hrs stirring, a solution of ethyl bromoacetate (0.7 mL, 6 mmol) in ether (4 mL) was added. The solution was stirred at 0° C. for 2 hrs, then warmed to room temperature for 3 hrs. The reaction was quenched with 10% HCl aqueous then the insoluble was filtered off. The organic layer was washed with water, sodium bicarbonate aqueous, dried over MgSO4, filtered and concentrated. The crude was purified via silica gel column eluted with EtOAc in hexanes from 0 to 10% to give light yellow solid (0.45 g, yield: 22% yield). ESI-MS: 369.20 (M+H)+.

1. additiontreated with copper(I) bromide-dimethyl sulfide complex (0.8 g, 3.9 mmol)
2. stirringAfter 2 hrs stirring
3. stirringThe solution was stirred at 0° C. for 2 hrs
4. temperaturewarmed to room temperature for 3 hrs
5. customThe reaction was quenched with 10% HCl aqueous
6. filtrationthe insoluble was filtered off
7. washThe organic layer was washed with water, sodium bicarbonate aqueous
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated
11. customThe crude was purified via silica gel column
12. washeluted with EtOAc in hexanes from 0 to 10%