Reacción #1934303

Ecuación de reacción

ammonium chloride

N,N-diisopropylethylamine

chloromethylmethyl ether

7-dehydrocholesterol

→

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

Rendimiento 89.0%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat room temperature
2. 2
   Extracciónfollowed by extraction with chloroform twice
3. 3
   LavadoThe organic layer was washed with saturated brine
4. 4
   Secadodried over anhydrous magnesium sulfate
5. 5
   Concentraciónconcentrated under reduced pressure
6. 6
   Otroto yield a residue
7. 7
   OtroThe residue was purified by silica gel column chromatography

Procedimiento

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%).

Fuente