반응 #1519112

반응 방정식

THF

4-(S)-benzyloxazolidin-2-one

n-BuLi

hexane

THF

→

N-hexanoyl-4-(S)-benzyloxazolidin-2-one

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture is stirred at −78° C. for 2 hours
2. 2
   온도to warm to rt
3. 3
   workup.STIRRINGstirred overnight
4. 4
   기타The reaction is then quenched with aqueous saturated NH4Cl
5. 5
   추출extracted with EtOAc
6. 6
   기타dried
7. 7
   기타purified by silica gel chromatography (hexanes/EtOAc)

실험 절차

To a solution of 4-(S)-benzyloxazolidin-2-one (56 mmol) (Aldrich, Milwaukee, Wis.) in THF at −78° C. is added 2.5 M n-BuLi in hexane (22:4 mL, 56 mmol) and the reaction is stirred at −78° C. for 2 hours. To this is added via cannula a −78° C. solution of acid chloride A-1 (R=hexanoyl, 65 mmol) in THF and the mixture is stirred at −78° C. for 2 hours, then allowed to warm to rt and stirred overnight. The reaction is then quenched with aqueous saturated NH4Cl, extracted with EtOAc, dried and purified by silica gel chromatography (hexanes/EtOAc) to afford N-hexanoyl-4-(S)-benzyloxazolidin-2-one (A-2).

출처