反応 #598914

反応方程式

cholesterol

triethylamine

3,5-dinitrobenzoylchloride

→

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

収率 56.4%

溶媒

dichloromethane

dichloromethane

反応条件

後処理

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
   その他the reaction mixture is partitioned between dichloromethane and water
5. 5
   洗浄The organic phase is washed repeatedly with water
6. 6
   乾燥dried over sodium sulfate
7. 7
   ろ過filtrated
8. 8
   濃縮concentrated under reduced pressure
9. 9
   その他Crystallization from ethyl acetate

実験手順

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.

出典