반응 #61114

반응 방정식

oxazolidinone

n-butyllithium

(S)-(+)-4-phenyl-2-oxazolidinone

Triethylamine

(S)-3-phenylbutyric acid

pivaloyl chloride

→

(S)-4-phenyl-3-((S)-3-phenyl-butyryl)-oxazolidin-2-one

수율 88.0%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   기타to give a white solid
2. 2
   온도then cooled back down to −78° C
3. 3
   workup.STIRRINGstirring
4. 4
   workup.WAITcontinued for 2 hours
5. 5
   기타The reaction was quenched with water (25 mL)
6. 6
   추출extracted with ethyl acetate
7. 7
   세척The combined extracts were washed with water, brine
8. 8
   건조dried over sodium sulfate
9. 9
   기타The crude product was purified by chromatography over silica gel
10. 10
    세척eluted with 2:3 ethyl acetate/hexanes
11. 11
    기타the resulting solid was recrystallized from ethyl acetate/hexanes

실험 절차

Triethylamine (1.3 mL, 9.1 mmol) was added to (S)-3-phenylbutyric acid (1.0 g, 6.1 mmol) in anhydrous tetrahydrofuran (60 mL) at −78° C. followed by the dropwise addition of pivaloyl chloride (0.83 ml, 6.7 mmol) to give a white solid. The reaction was allowed to warm to room temperature for 10 minutes then cooled back down to −78° C. In a separate flask, n-butyllithium (4.6 mL, 11.6 mmol, 2.5 M F in hexanes) was added to (S)-(+)-4-phenyl-2-oxazolidinone (2.0 g, 12.2 mmol) in anhydrous tetrahydrofuran at −78° C. and allowed to stir for 10 minutes. The lithiated oxazolidinone was transfered via cannula to the mixed anhydride at −78° C. and stirring continued for 2 hours. The reaction was quenched with water (25 mL) and extracted with ethyl acetate. The combined extracts were washed with water, brine and dried over sodium sulfate. The crude product was purified by chromatography over silica gel eluted with 2:3 ethyl acetate/hexanes and the resulting solid was recrystallized from ethyl acetate/hexanes to afford (S)-4-phenyl-3-((S)-3-phenyl-butyryl)-oxazolidin-2-one (1.63 g, 88% yield).

출처