反应 #598914

反应方程式

cholesterol

triethylamine

3,5-dinitrobenzoylchloride

→

(3-β)-cholest-5-en-3-yl 3,5-dinitrobenzoate

收率 56.4%

溶剂

dichloromethane

dichloromethane

反应条件

后处理

1. 1
   workup.ADDITIONare added at 0° C
2. 2
   workup.STIRRINGto stir at room temperature overnight
3. 3
   workup.WAITAfter 22 hours at room temperature
4. 4
   其他the reaction mixture is partitioned between dichloromethane and water
5. 5
   洗涤The organic phase is washed repeatedly with water
6. 6
   干燥dried over sodium sulfate
7. 7
   过滤filtrated
8. 8
   浓缩concentrated under reduced pressure
9. 9
   其他Crystallization from ethyl acetate

实验过程

20.00 g (51.7 mmol) of cholesterol, 2.88 g (25.75 mmol) of 4-dimethylaminopyridine, 6.27 g (62.04 mmol) of triethylamine are dissolved in 100 mL of dichloromethane. 11.92 g (51.7 mmol) of commercial 3,5-dinitrobenzoylchloride dissolved in 50 mL of dichloromethane are added at 0° C. The solution is stirred for 2 h at 0° C. and allowed to stir at room temperature overnight. After 22 hours at room temperature, the reaction mixture is partitioned between dichloromethane and water. The organic phase is washed repeatedly with water, dried over sodium sulfate, filtrated and concentrated under reduced pressure. Crystallization from ethyl acetate:hexane mixture yielded 16.94 g (56%) of (3-β)-cholest-5-en-3-yl 3,5-dinitrobenzoate as yellowish crystals.

来源