Reaktion #81468

Reaktionsgleichung

triethylammonium chloride

triethylamine

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

acetyl chloride

→

title compound

Ausbeute 84.3%

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

Ausbeute 84.3%

Lösungsmittel

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigehad formed
2. 2
   FiltrationThe mixture was then filtered
3. 3
   Einengenthe filtrate concentrated
4. 4
   Sonstigeto afford the crude product which
5. 5
   Sonstigewas recrystallised firstly from ethanol/water (1:1)

Vorschrift

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%).

Quelle