Reacción #598914

Ecuación de reacción

cholesterol

triethylamine

3,5-dinitrobenzoylchloride

→

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

Rendimiento 56.4%

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

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
   Otrothe reaction mixture is partitioned between dichloromethane and water
5. 5
   LavadoThe organic phase is washed repeatedly with water
6. 6
   Secadodried over sodium sulfate
7. 7
   Filtraciónfiltrated
8. 8
   Concentraciónconcentrated under reduced pressure
9. 9
   OtroCrystallization from ethyl acetate

Procedimiento

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.

Fuente