反应详情

温度

-78 °C

To a cooled (−78° C.) solution of (R)-4-benzyl-3-pent-4-enoyl-oxazolidin-2-one (0.500 g, 1.928 mmol) in 15 mL of THF, was added LiHMDS (2.9 mL, 2.9 mmol, 1.0 M in THF). The resulting mixture was stirred at −78° C. under N2 for 1 h and then a solution of 3,5-dimethyl-4-fluorobenzyl bromide (0.460 g, 2.121 mmol) in 5 mL of THF was added. After being stirred at −78° C. for 1 h followed by warming to room temperature over 2 h, the reaction mixture was quenched with 50 mL of aqueous NH4Cl solution and extracted with dichloromethane (50 mL×3). The combined organic extracts were dried, filtered, and concentrated under reduced pressure. The product was isolated by Flash column chromatography (silica gel) eluting with 0-100% dichloromethane/hexanes to give the title compound as colorless oil (0.221 g, 56% yield). GC-MS: tR=7.0 min; m/z 395 (M+).

1. stirringAfter being stirred at −78° C. for 1 h
2. temperatureby warming to room temperature over 2 h
3. customthe reaction mixture was quenched with 50 mL of aqueous NH4Cl solution
4. extractionextracted with dichloromethane (50 mL×3)
5. customThe combined organic extracts were dried
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe product was isolated by Flash column chromatography (silica gel)
9. washeluting with 0-100% dichloromethane/hexanes