Reaktion #1934303

Reaktionsgleichung

ammonium chloride

N,N-diisopropylethylamine

chloromethylmethyl ether

7-dehydrocholesterol

→

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

Ausbeute 89.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat room temperature
2. 2
   Extraktionfollowed by extraction with chloroform twice
3. 3
   WaschenThe organic layer was washed with saturated brine
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   Sonstigeto yield a residue
7. 7
   SonstigeThe residue was purified by silica gel column chromatography

Vorschrift

Commercially available 7-dehydrocholesterol (18.3 g, 47.6 mmol) was dissolved in dichloromethane (150 mL), and N,N-diisopropylethylamine (24.9 mL, 143 mmol) and chloromethylmethyl ether (7.23 mL, 95.2 mmol) were added thereto at room temperature, followed by stirring overnight. 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 (S)-3-methoxymethoxy-5,7-cholestadiene (18.1 g, 89%).

Quelle