Dimethyl Sulfate → 1,3-Dimethoxyestra-1,3,5(10)-trien-17-one

HRID 839760Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 839760
[OH:1][C:2]1[C:19]2[C@@H:18]3[C@H:9]([C@H:10]4[C@@:14]([CH2:16][CH2:17]3)([CH3:15])[C:13](=[O:20])[CH2:12][CH2:11]4)[CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([O:21][CH3:22])[CH:3]=1.S(OC)(O[CH3:27])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:27][O:1][C:2]1[C:19]2[C@@H:18]3[C@H:9]([C@H:10]4[C@@:14]([CH2:16][CH2:17]3)([CH3:15])[C:13](=[O:20])[CH2:12][CH2:11]4)[CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([O:21][CH3:22])[CH:3]=1

Komponenten

5

Edukt 3

HCID 6497Dimethyl Sulfate2×HCID 11430Potassium CarbonateHCID 545489061-Hydroxy-3-methoxyestra-1,3,5(10)-trien-17-one

Produkt 1

HCID 537114841,3-Dimethoxyestra-1,3,5(10)-trien-17-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A suspension of 1-hydroxy-3-methoxyestra-1,3,5(10)-trien-17-one (2.5 g, 8.3 mM), dimethyl sulfate (1.3 g, 10.3 mM) and potassium carbonate (1.2 g) in 250 ml of anhydrous acetone is refluxed with vigorous stirring for 6 hrs. An additional 0.5 g of dimethyl sulfate is added and the suspension refluxed for 14 hrs. The reaction mixture is filtered while warm and the solids washed well with acetone. The combined acetone filtrates are evaporated in vacuo and the residue is recrystallized from methanol-H2O. Two recrystallizations give 1,3-dimethoxyestra-1,3,5(10)-trien-17-one, yield 1.91 g (73%); m.p. 132°-133°.

Aufarbeitung

  1. temperatureis refluxed
  2. temperaturethe suspension refluxed for 14 hrs
  3. filtrationThe reaction mixture is filtered
  4. temperaturewhile warm
  5. washthe solids washed well with acetone
  6. customThe combined acetone filtrates are evaporated in vacuo
  7. customthe residue is recrystallized from methanol-H2O
  8. customTwo recrystallizations

Quellen und Nachweise

ORD-Eintrag
ord-4424f8ccdde842ada0fad0c8f77c8924
Quelldatensatz
uspto-grants-1978_06
Patentnummer
US04096253

Notizen zur Reaktion

Wird geladen…