반응 #2195477

반응 방정식

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

Sodium hydride

Linoleyl mesylate

→

colorless oil

수율 81.0%

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

수율 81.0%

용매

toluene

반응 조건

후처리

1. 1
   workup.ADDITIONA stir bar was added to the flask, which
2. 2
   기타was then sealed
3. 3
   기타flushed with argon
4. 4
   workup.ADDITIONcharged with anhydrous toluene (100 mL)
5. 5
   workup.ADDITIONadded slowly to the reaction mixture
6. 6
   기타The flask was fitted with a reflux condenser
7. 7
   기타the apparatus was flushed with argon
8. 8
   온도The reaction mixture was heated in an oil bath
9. 9
   workup.STIRRINGto stir
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    온도at reflux overnight
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    workup.ADDITIONethanol was added dropwise until gas evolution
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    workup.ADDITIONThe reaction mixture was diluted with ethyl acetate (300 mL)
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    세척washed with aqueous 10% sodium carbonate (2×200 mL)
14. 14
    추출back extracted with ethyl acetate (2×100 mL)
15. 15
    건조dried over MgSO4
16. 16
    여과filtered
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    농축concentrated
18. 18
    기타The resultant oil was purified via column chromatography (10% EtOAc/Hexanes, 3% TEA)

실험 절차

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.

출처