Reacción #1934287

Ecuación de reacción

ammonium chloride

imidazole

chlorotriethylsilane

7-dehydrocholesterol

→

title compound

Rendimiento 87.1%

(S)-3-Triethylsiloxy-5,7-cholestadiene

Rendimiento 87.1%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónfollowed by extraction with chloroform twice
2. 2
   LavadoThe organic layer was washed with saturated brine
3. 3
   Secadodried over anhydrous magnesium sulfate
4. 4
   Concentraciónconcentrated under reduced pressure
5. 5
   Otroto yield a residue
6. 6
   OtroThe residue was purified by silica gel column chromatography

Procedimiento

Commercially available 7-dehydrocholesterol (10.6 g, 27.6 mmol) was dissolved in dichloromethane (90 mL), and then imidazole (3.75 g, 55.1 mmol) and chlorotriethylsilane (6.94 mL, 41.3 mmol) were added at room temperature, followed by stirring for 12 hours. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with chloroform twice. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to yield a residue. The residue was purified by silica gel column chromatography to obtain the title compound (12.0 g, 87%).

Fuente