反应 #2195477

反应方程式

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

Sodium hydride

Linoleyl mesylate

→

colorless oil

收率 81.0%

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

收率 81.0%

溶剂

toluene

反应条件

后处理

1. 1
   workup.ADDITIONA stir bar was added to the flask, which
2. 2
   其他was then sealed
3. 3
   其他flushed with argon
4. 4
   workup.ADDITIONcharged with anhydrous toluene (100 mL)
5. 5
   workup.ADDITIONadded slowly to the reaction mixture
6. 6
   其他The flask was fitted with a reflux condenser
7. 7
   其他the apparatus was flushed with argon
8. 8
   温度The reaction mixture was heated in an oil bath
9. 9
   workup.STIRRINGto stir
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    温度at reflux overnight
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    workup.ADDITIONethanol was added dropwise until gas evolution
12. 12
    workup.ADDITIONThe reaction mixture was diluted with ethyl acetate (300 mL)
13. 13
    洗涤washed with aqueous 10% sodium carbonate (2×200 mL)
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    萃取back extracted with ethyl acetate (2×100 mL)
15. 15
    干燥dried over MgSO4
16. 16
    过滤filtered
17. 17
    浓缩concentrated
18. 18
    其他The resultant oil was purified via column chromatography (10% EtOAc/Hexanes, 3% TEA)

实验过程

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.

来源