Reaktion #1934287

Reaktionsgleichung

ammonium chloride

imidazole

chlorotriethylsilane

7-dehydrocholesterol

→

title compound

Ausbeute 87.1%

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

Ausbeute 87.1%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionfollowed by extraction with chloroform twice
2. 2
   WaschenThe organic layer was washed with saturated brine
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   Sonstigeto yield a residue
6. 6
   SonstigeThe residue was purified by silica gel column chromatography

Vorschrift

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%).

Quelle