反应详情

温度

45 °C

To a slurry of NaH (22 g of 60% NaH in mineral oil, 0.55 mol) in 400 mL benzene was added the product of Example 1A (0.387 mol) in 100 mL benzene dropwise via addition funnel. The mixture stirred for 30 minutes after the addition was complete, then was warmed to reflux and allowed to stir for 1.5 h. The reaction was cooled to 45° C. and stirred for 16 h. A portion of benzyl bromide (45 mL, 0.38 mol) was added, the mixture was warmed to reflux and an additional amount of benzyl bromide was added (45 mL, 0.38 mol). This solution stirred for 24 h at reflux, then was cooled to ambient temperature, filtered through Celite® diatomaceous earth and the residue was washed with CH2Cl2. The combined filtrates were concentrated under reduced pressure and excess benzyl bromide was removed via distillation. The distillation residue was purified via column chromatography (SiO2, 75% hexanes-EtOAc) to give 46.6 g of the title compound (0.2 mol, 52% yield). MS (DCl/NH3) m/z 234 (M+H)+.

1. additiondropwise via addition funnel
2. additionafter the addition
3. temperaturewas warmed
4. temperatureto reflux
5. stirringto stir for 1.5 h
6. stirringstirred for 16 h
7. temperaturethe mixture was warmed
8. temperatureto reflux
9. stirringThis solution stirred for 24 h
10. temperatureat reflux
11. temperaturewas cooled to ambient temperature
12. filtrationfiltered through Celite® diatomaceous earth
13. washthe residue was washed with CH2Cl2
14. concentrationThe combined filtrates were concentrated under reduced pressure and excess benzyl bromide
15. customwas removed via distillation
16. distillationThe distillation residue was purified via column chromatography (SiO2, 75% hexanes-EtOAc)