反应详情

温度

-78 °C

Cool a solution of (R)-4-Benzyl-3-pent-4-enoyl-oxazolidin-2-one (4.8 g, 19 mmol) in THF (100 mL) to −78° C. Treat the solution dropwise with 10M LiHMDS in THF (20 mL, 20 mmol) and stir at −78° C. for 30 minutes. Treat the solution with 5-Benzyloxy-2-bromomethyl-1,3-dimethyl-benzene (6.8 g, 22 mmol) and allow to slowly warm to room temperature. The reaction stirs 3 hr at room temperature. Quench the reaction with 1N HCl (aqueous) and extract with Et2O. Wash the organic with brine, dry over MgSO4, filter, and remove the solvent. Purify the crude by silica gel column chromatography using Hexanes:EtOAc to elute the pure product. Remove the solvent to afford 7.0 g (78%) of desired product. MS (m/e): 484 (M+1).

1. temperatureto slowly warm to room temperature
2. waitThe reaction stirs 3 hr at room temperature
3. customQuench
4. customthe reaction with 1N HCl (aqueous)
5. extractionextract with Et2O
6. washWash the organic with brine
7. dry with materialdry over MgSO4
8. filtrationfilter
9. customremove the solvent
10. customPurify the crude by silica gel column chromatography
11. washEtOAc to elute the pure product
12. customRemove the solvent