Reaktion #1270070

Reaktionsgleichung

androst-5-ene-3,17-dione

AcOH

→

4α-acetoxyandrost-5-ene-3,17-dione

Ausbeute 25.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred for 24 h
2. 2
   SonstigeThe reaction was quenched by addition of H2O
3. 3
   Extraktionextracted three times with EtOAc
4. 4
   WaschenThe combined organic extracts were washed with H2O, brine
5. 5
   Trocknendried over Na2SO4
6. 6
   Sonstigeevaporated to dryness
7. 7
   SonstigeThe crude product was purified
8. 8
   Sonstigeby triturating with a 1:1 mixture of n-hexane

Vorschrift

To a solution of androst-5-ene-3,17-dione (2.00 g) in toluene (10 ml) at 15° C., AcOH (10 ml) and LTA (3.40 g) were added. After stirring for 2 h, the mixture was warmed to RT and stirred for 24 h. The reaction was quenched by addition of H2O and extracted three times with EtOAc. The combined organic extracts were washed with H2O, brine, dried over Na2SO4, and evaporated to dryness. The crude product was purified by triturating with a 1:1 mixture of n-hexane:EtOAc (3 ml) to give 4α-acetoxyandrost-5-ene-3,17-dione (600 mg, 25%).

Quelle