Réaction #2075685

Équation de réaction

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

Sodium hydride

Linoleyl mesylate

→

colorless oil

Rendement 81.0%

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

Rendement 81.0%

Solvants

toluene

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONA stir bar was added to the flask, which
2. 2
   Autrewas then sealed
3. 3
   Autreflushed with argon
4. 4
   workup.ADDITIONcharged with anhydrous toluene (100 mL)
5. 5
   workup.ADDITIONadded slowly to the reaction mixture
6. 6
   AutreThe flask was fitted with a reflux condenser
7. 7
   Autrethe apparatus was flushed with argon
8. 8
   TempératureThe reaction mixture was heated in an oil bath
9. 9
   workup.STIRRINGto stir
10. 10
    Températureat 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
    Lavagewashed with aqueous 10% sodium carbonate (2×200 mL)
14. 14
    Extractionback extracted with ethyl acetate (2×100 mL)
15. 15
    Séchagedried over MgSO4
16. 16
    Filtrationfiltered
17. 17
    Concentrationconcentrated
18. 18
    AutreThe resultant oil was purified via column chromatography (10% EtOAc/Hexanes, 3% TEA)

Mode opératoire

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.

Source