Réaction #1519112

Équation de réaction

THF

4-(S)-benzyloxazolidin-2-one

n-BuLi

hexane

THF

→

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

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source