Reacción #81468

Ecuación de reacción

triethylammonium chloride

triethylamine

17-(3-pyridyl)androsta-5,16-dien-3β-ol

acetyl chloride

→

title compound

Rendimiento 84.3%

3β-Acetoxy-17-(3-pyridyl)androsta-5,16-diene

Rendimiento 84.3%

Disolventes

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrohad formed
2. 2
   FiltraciónThe mixture was then filtered
3. 3
   Concentraciónthe filtrate concentrated
4. 4
   Otroto afford the crude product which
5. 5
   Otrowas recrystallised firstly from ethanol/water (1:1)

Procedimiento

To a stirred suspension of finely powdered 17-(3-pyridyl)androsta-5,16-dien-3β-ol (3.50 g, 10 mmol) in dry diethyl ether (150 ml) coning triethylamine (2,3 ml, 16 mmol) and dimethylaminopyridine (0.012 g, 0.1 mmol) was added acetyl chloride (1.0 ml, 14 mmol). The mixture was then stirred at ambient temperature for 12 h, over which time a thick whim precipitate of triethylammonium chloride had formed. The mixture was then filtered and the filtrate concentrated to afford the crude product which was recrystallised firstly from ethanol/water (1:1), then finally from hexane to afford the title compound (3.30 g, 84%).

Fuente