Reaktion #84678

Reaktionsgleichung

(4R)-4-(phenylmethyl)-1,3-oxazolidin-2-one

n-BuLi

4-pentenoyl chloride

→

title compound

Ausbeute 93.0%

(R)-4-benzyl-3-pent-4-enoyloxazolidin-2-one

Ausbeute 93.0%

Lösungsmittel

THF

THF

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat −78° C.
2. 2
   workup.STIRRINGAfter stirring at −78° C. for another 1 hour
3. 3
   Temperaturto warm up to room temperature
4. 4
   workup.STIRRINGstirred overnight
5. 5
   Extraktionthe mixture was extracted with ethyl acetate (2×400 mL)
6. 6
   WaschenThe combined ethyl acetate extracts were washed with brine
7. 7
   Trocknendried over sodium sulfate
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated under reduced pressure
10. 10
    SonstigeThe crude residue was purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:10)

Vorschrift

To a solution of (4R)-4-(phenylmethyl)-1,3-oxazolidin-2-one (50 g, 282 mmol) in THF (300 mL) was dropwise added n-BuLi in THF (2.4 M, 176 mL, 423 mmol) under nitrogen at −78° C., and the resulting mixture was stirred at −78° C. for 1 hour. Then 4-pentenoyl chloride (49 mL, 423 mmol) was dropwise added. After stirring at −78° C. for another 1 hour, the reaction mixture was allowed to warm up to room temperature and stirred overnight. After diluting with water, the mixture was extracted with ethyl acetate (2×400 mL). The combined ethyl acetate extracts were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:10) to afford the title compound (68 g, 93%) as a light yellow oil. MS (ES+) C15H17NO3 requires: 259, found: 260 [M+H]+.

Quelle