Thioglycolic Acid → 11beta-Hydroxyandrost-4-ene-3,17-dione

HRID 1659457

Reaktionsgleichung

Reaktionsgleichung von HRID 1659457
Br[C@:2]12[C@@H:19]([OH:20])[CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH2:14][C:15]3=[O:21])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:23])[CH2:4][CH2:5][C:6](=[O:22])[CH:7]=1.C(O)(=O)CS>C1COCC1.O>[OH:20][C@H:19]1[CH2:18][C@@:16]2([CH3:17])[C@@H:12]([CH2:13][CH2:14][C:15]2=[O:21])[C@H:11]2[C@H:2]1[C@:3]1([CH3:23])[C:8]([CH2:9][CH2:10]2)=[CH:7][C:6](=[O:22])[CH2:5][CH2:4]1

Komponenten

5

Edukt 2

HCID 1133Thioglycolic AcidHCID 111326859alpha-Bromo-11beta-hydroxy-4-androstene-3,17-dione

Produkt 1

HCID 9414111beta-Hydroxyandrost-4-ene-3,17-dioneAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 9α-bromo-11β-hydroxyandrost-4-ene-3,17-dione (III, 2.00 g), thioglycolic acid (2.0 ml) in THF (20 ml) and water (5 ml) is stirred under nitrogen at 20°-25°. A chromous sulfate solution (1.4 M, 5.5 ml) is added and the two-phase system is stirred. After four hours, another 4.5 ml of chromous sulfate solution is added and the mixture stirred overnight. The mixture is diluted with water and extracted with ethyl acetate. The ethyl acetate extracts are washed with water, a diluted sodium hydroxide solution, water and saline. The organic phase is dried over sodium sulfate and concentrated to a solid. The solid is crystallized from benzene-hexane to give a first crop of crystals of the title compound (1.38 g, 83.5% chemical yield) which are measured to be 99% pure as measured by GLC and is identical to an authentic sample.

Aufarbeitung

  1. stirringthe mixture stirred overnight
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate extracts are washed with water
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. concentrationconcentrated to a solid
  6. customThe solid is crystallized from benzene-hexane

Quellen und Nachweise

ORD-Eintrag
ord-301131bbee3b46aca2ddd5fdb22772e3
Quelldatensatz
uspto-grants-1981_12
Patentnummer
US04304727

Verknüpfte Notizen

Wird geladen…