反应详情

温度

-78 °C

To a 2 L three-necked round bottom flask was added cyclobutanone (12.47 g, 178 mmol) and THF (1200 mL). The solution was cooled to −78° C. Allylmagnesium bromide, 1 M in ether (196 ml, 196 mmol) was added via an addition funnel over 30 min. The reaction was allowed to stir for 30 min. MeOH (30 mL) was added to the reaction and the cooling bath was removed. The solution was stirred for about 10 min, then HCl (0.5 M, 500 mL) was added. The reaction was transferred to a separatory funnel and extracted with Ether (2×1 L). The organic extracts were dried over MgSO4 and concentrated in vacuo (Note: Volatile Product). The final ˜100 mL of concentrate were re-dissolved in 1 L of DCM, dried over MgSO4 and filtered. TEA (61.5 ml, 442 mmol) was added followed by tert-butyldimethylsilyl triflate (66.0 ml, 287 mmol). The reaction was cooled in the warming dry ice bath used earlier in the experiment. After 30 min, the reaction was checked by TLC and found to be complete. HCl (0.5 M, 500 mL) was added to quench the reaction. The reaction layers were separated and the aqueous layer extracted with 600 mL of ether. The combined organic layers were dried over MgSO4 and concentrated in vacuo. The resulting oil was loaded onto a 600 mL Frit almost full of silica gel and purified, eluting with 1400 mL of hexane. The hexane filtrate was carefully concentrated in vacuo to give (1-allylcyclobutoxy)(tert-butyl)dimethylsilane, as a colorless liquid that also contained residual hexane. The crude material was carried on without further purification.

1. customthe cooling bath was removed
2. stirringThe solution was stirred for about 10 min
3. additionHCl (0.5 M, 500 mL) was added
4. customThe reaction was transferred to a separatory funnel
5. extractionextracted with Ether (2×1 L)
6. dry with materialThe organic extracts were dried over MgSO4
7. concentrationconcentrated in vacuo (Note: Volatile Product)
8. concentrationThe final ˜100 mL of concentrate
9. dissolutionwere re-dissolved in 1 L of DCM
10. dry with materialdried over MgSO4
11. filtrationfiltered
12. waitAfter 30 min
13. customto quench
14. customthe reaction
15. customThe reaction layers were separated
16. extractionthe aqueous layer extracted with 600 mL of ether
17. dry with materialThe combined organic layers were dried over MgSO4
18. concentrationconcentrated in vacuo
19. custompurified
20. washeluting with 1400 mL of hexane
21. concentrationThe hexane filtrate was carefully concentrated in vacuo