反应详情

温度

-78 °C

A mechanically stirred solution of the resultant compound from Example 64 (10 g, 56.4 mmol) in dry THF (200 ml) under an atmosphere of nitrogen was treated with n-butyl-lithium in hexanes (1.05 equiv, 22.6 ml, 56.4 mmol, 2.5M) at -78° C. After stirring for an additional 20 min at -78° C., hydrocinnamoyl chloride (9.4 ml, 62 mmol, 1.1 equiv) was added and the reaction was allowed to warm to room temperature with stirring over 2 h. The clear reaction mixture was poured into 100 ml of saturated NH4Cl. The organic layer was removed and the resulting aqueous layer extracted three times with dichloromethane. The combined organic extracts were washed once with brine, dried (anhydrous sodium sulfate), filtered, and concentrated under reduced pressure to afford a crude solid. This material was recrystallized from hot ethyl acetate/hexane at 0°-5° C. overnight. First crop yielded 12.9 g, mp 99°-100° C. Second crop afforded 3.6 g. Total yield 16.5 g (95%).

1. temperatureto warm to room temperature
2. stirringwith stirring over 2 h
3. customThe organic layer was removed
4. extractionthe resulting aqueous layer extracted three times with dichloromethane
5. washThe combined organic extracts were washed once with brine
6. dry with materialdried (anhydrous sodium sulfate)
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customto afford a crude solid
10. customThis material was recrystallized from hot ethyl acetate/hexane at 0°-5° C. overnight
11. customFirst crop yielded 12.9 g, mp 99°-100° C
12. customSecond crop afforded 3.6 g