Acetic Acid → HCID 68729360, Verbindung
Reaktionsgleichung
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH:9]=[C:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[CH2:11]4)[C@@H:6]1[CH2:5][CH2:4][C:3]2=[O:21].[CH3:22][C:23]([OH:25])=[O:24]>C1(C)C=CC=CC=1>[C:23]([O:25][C@@H:11]1[C:12](=[O:20])[CH2:13][CH2:14][C@@:15]2([CH3:16])[C:10]1=[CH:9][CH2:8][C@@H:7]1[C@@H:17]2[CH2:18][CH2:19][C@@:2]2([CH3:1])[C@H:6]1[CH2:5][CH2:4][C:3]2=[O:21])(=[O:24])[CH3:22]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
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%).