Phosphoric Acid → 9-Dehydroandrostenedione

HRID 1087678

Reaktionsgleichung

Reaktionsgleichung von HRID 1087678
O[C@:2]12[CH2:19][CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH2:14][C:15]3=[O:20])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:22])[CH2:4][CH2:5][C:6](=[O:21])[CH:7]=1.P(=O)(O)(O)O>O>[CH3:17][C@:16]12[CH2:18][CH:19]=[C:2]3[C@@H:11]([CH2:10][CH2:9][C:8]4[C@:3]3([CH3:22])[CH2:4][CH2:5][C:6](=[O:21])[CH:7]=4)[C@@H:12]1[CH2:13][CH2:14][C:15]2=[O:20]

Komponenten

4

Edukt 2

HCID 1004Phosphoric AcidHCID 104250179alpha-Hydroxyandrost-4-ene-3,17-dione

Produkt 1

HCID 2395959-Dehydroandrostenedione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

9α-Hydroxyandrostenedione (280 mg.; 302 mg. of 92.7% purity) is added to phosphoric acid (85%, 5 ml.) and stirred at 35°-48° for 7.5 hours. Water (10 ml.) is then added, the mixture stirred and filtered. The solids are air-dried at 25° for 10 hours to give androsta-4,9(11)-diene-3,17-dione, 254 mg. (90.7% weight yield, 96.2% chemical yield); m.p. 197°-201°. GC (Example 1) shows an androsta-4,9(11)-diene-3,17-dione/androsta-4,8-diene-3,17-dione ratio greater than 99 to 1.

Aufarbeitung

  1. stirringthe mixture stirred
  2. filtrationfiltered
  3. customThe solids are air-dried at 25° for 10 hours

Quellen und Nachweise

ORD-Eintrag
ord-0add41fbe6454ad9b178403b89f5016f
Quelldatensatz
uspto-grants-1990_10
Patentnummer
USRE033364

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