Reaktion #930388

Reaktionsgleichung

14,15-epoxide

3β, 12β-Dihydroxy-14,15-epoxy-20,20-ethylenedioxypregn-5-ene

lithium aluminium hydride

water

sodium hydroxide

→

trihydroxy pregnene

Ausbeute 83.0%

3β, 12β, 14β-Trihydroxy-20,20-ethylenedioxypregn-5-ene

Ausbeute 83.0%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction refluxed for 48 h
2. 2
   Filtration0,3 ml) and filtration
3. 3
   Sonstigethe mixture is purified by silica gel column chromatography

Vorschrift

The 14,15-epoxide (24) (300 mg, 0,77 mmol) in dry tetrahydrofuran (10 ml) is added to a suspension of lithium aluminium hydride (300 mg, 7,89 mmol) in tetrahydrofuran and the reaction refluxed for 48 h. After the addition of water (0,3 ml), sodium hydroxide (15% soln, 0,3 ml) and filtration as described earlier, the mixture is purified by silica gel column chromatography using methanol: chloroform (1:9) as solvent to give the trihydroxy pregnene (25) (250 mg, 83%).

Quelle