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Acetic Acid → 7alpha-Methylestr-4-ene-3,11,17-trione

HRID 637618
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 637618
[OH:1][C@@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C@@H:4]1[C:9]([CH2:10][C@H:11]2[CH3:21])=[CH:8][C:7](=[O:22])[CH2:6][CH2:5]1.C(O)(=O)C.S(=O)(=O)(O)O.C>O.C(OCC)(=O)C.C(Cl)Cl.O.S([O-])([O-])(=O)=O.[Mn+2].[O-2].[O-2].[O-2].[Cr+6]>[CH3:21][C@@H:11]1[CH2:10][C:9]2[C@H:4]([CH2:5][CH2:6][C:7](=[O:22])[CH:8]=2)[C@@H:3]2[C@@H:12]1[C@H:13]1[C@@:17]([CH2:19][C:2]2=[O:1])([CH3:18])[C:16](=[O:20])[CH2:15][CH2:14]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 4

HCID 176Acetic AcidHCID 297MethaneHCID 1118Sulfuric AcidHCID 1202027311alpha-Hydroxy-7alpha-methylestr-4-ene-3,17-dione

Produkt 1

HCID 572776857alpha-Methylestr-4-ene-3,11,17-trione

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 962
Water
Katalysator
HCID 177577Manganese sulfate monohydrateKatalysator
HCID 10219390chromium (VI) trioxideKatalysator2×
HCID 962WaterLösungsmittel3×
HCID 21226138Dichloromethane ethylacetateLösungsmittel

Versuchsvorschrift

A mixture of 11α-hydroxy-7α-methylestr-4-ene-3,17-dione (A, obtained from Fermentation) and acetic acid (7.5 ml) is stirred and cooled to about 10° in a cold water bath. The following reagents are added: water (6 drops), manganese sulfate monohydrate (0.1 g) in water (1 ml), chromium trioxide (0.66 g) in water (2 ml), and concentrated sulfuric acid (0.6 ml). The chromium trioxide solution is added over a 15 minute period. After 1/2 hour water (10 ml) is added and the crystals of the product are collected, washed with water and dried to give a solid. The solid is dissolved in hot ethyl acetate/methylene chloride (1/1) and decolorized with a little charcoal and silica gel and then filtered through celite. The appropriate fractions are pooled and concentrated to give crystals, UV (ethyl alcohol) λmax =239 nm (ε=16250); IR (mull) 1740, 1707, 1672 and 1616; MS (m/e)=300, 282, 272, and 258.

Aufarbeitung

  1. temperaturecooled to about 10° in a cold water bath
  2. additionThe following reagents are added
  3. customthe crystals of the product are collected
  4. washwashed with water
  5. customdried
  6. customto give a solid
  7. filtrationfiltered through celite
  8. concentrationconcentrated
  9. customto give crystals, UV (ethyl alcohol) λmax =239 nm (ε=16250)

Quellen und Nachweise

ORD-Eintrag
ord-ef76c2cfb25c45848d5eb8ad055c7b8e
Quelldatensatz
uspto-grants-1985_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04557867

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