Reaktion #2075685

Reaktionsgleichung

3-Dimethylamino-2-(Cholest-5-en-3β-oxybutan-4-oxy)-1-propanol

Sodium hydride

Linoleyl mesylate

→

colorless oil

Ausbeute 81.0%

3-Dimethylamino-2-(cholest-5-en-3β-oxybutan-4-oxy)-1-(cis,cis-9,12-octadecadienoxy)propane

Ausbeute 81.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONA stir bar was added to the flask, which
2. 2
   Sonstigewas then sealed
3. 3
   Sonstigeflushed with argon
4. 4
   workup.ADDITIONcharged with anhydrous toluene (100 mL)
5. 5
   workup.ADDITIONadded slowly to the reaction mixture
6. 6
   SonstigeThe flask was fitted with a reflux condenser
7. 7
   Sonstigethe apparatus was flushed with argon
8. 8
   TemperaturThe reaction mixture was heated in an oil bath
9. 9
   workup.STIRRINGto stir
10. 10
    Temperaturat reflux overnight
11. 11
    workup.ADDITIONethanol was added dropwise until gas evolution
12. 12
    workup.ADDITIONThe reaction mixture was diluted with ethyl acetate (300 mL)
13. 13
    Waschenwashed with aqueous 10% sodium carbonate (2×200 mL)
14. 14
    Extraktionback extracted with ethyl acetate (2×100 mL)
15. 15
    Trocknendried over MgSO4
16. 16
    Filtrationfiltered
17. 17
    Einengenconcentrated
18. 18
    SonstigeThe resultant oil was purified via column chromatography (10% EtOAc/Hexanes, 3% TEA)

Vorschrift

3-Dimethylamino-2-(Cholest-5-en-3β-oxybutan-4-oxy)-1-propanol (2.6 g, 4.6 mmol) was weighed into a 200 mL round bottomed flask and co-evaporated with anhydrous toluene 2×20 mL). A stir bar was added to the flask, which was then sealed, flushed with argon and charged with anhydrous toluene (100 mL). Sodium hydride (0.7 g, 6 equiv) was added at once and the mixture was stirred, under argon, for 20 minutes. Linoleyl mesylate (4.6 g, 2.3 equiv.) was measured in a PP syringe and added slowly to the reaction mixture. The flask was fitted with a reflux condenser and the apparatus was flushed with argon. The reaction mixture was heated in an oil bath and allowed to stir at reflux overnight. The reaction mixture was then cooled to room temperature in a water bath and ethanol was added dropwise until gas evolution ceased. The reaction mixture was diluted with ethyl acetate (300 mL) and washed with aqueous 10% sodium carbonate (2×200 mL). The aqueous phases were combined and back extracted with ethyl acetate (2×100 mL). The organic phases were combined, dried over MgSO4, filtered and concentrated. The resultant oil was purified via column chromatography (10% EtOAc/Hexanes, 3% TEA) to afford 3.0 g (81%) of a colorless oil.

Quelle