Reacción #1934288

Ecuación de reacción

ammonium chloride

7-dehydrocholesterol

N,N-diisopropylethylamine

chloromethylmethylether

→

title compound

Rendimiento 85.2%

3-(Methoxymethyloxy)-cholest-5,7-diene

Rendimiento 85.2%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   Extracciónfollowed by extraction with ethyl acetate (100 mL×2)
3. 3
   LavadoThe organic layer was washed with dilute aqueous hydrochloric acid and saturated brine
4. 4
   Secadodried over anhydrous sodium sulfate
5. 5
   Concentraciónconcentrated
6. 6
   workup.ADDITIONTo the residue, methanol was added
7. 7
   Otroto triturate

Procedimiento

In dichloromethane (45 mL), 7-dehydrocholesterol (2.0 g, 5.2 mmol) was dissolved, then N,N-diisopropylethylamine (2.70 mL, 15.6 mmol) and chloromethylmethylether (1.00 mL, 13.2 mmol) were sequentially added under ice-cooling, followed by stirring at room temperature for 20 hours. The reaction mixture was poured into a saturated aqueous ammonium chloride solution, followed by extraction with ethyl acetate (100 mL×2). The organic layer was washed with dilute aqueous hydrochloric acid and saturated brine, dried over anhydrous sodium sulfate, and concentrated to yied a residue. To the residue, methanol was added to triturate to obtain the title compound (1.9 g, 83%).

Fuente