Sulfuric Acid → 3-Methoxyestra-1,3,5(10),9(11)-tetraen-17-one

HRID 437017

Reaktionsgleichung

Reaktionsgleichung von HRID 437017
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:19]2[C@H:9]3[CH2:10][CH2:11][C@@:12]4([CH3:18])[C@H:16]([C@@H:8]3[CH2:7][CH2:6][C:5]=2[CH:4]=1)[CH2:15][CH2:14][C:13]4=[O:17].C([O-])(=O)C.[Na+].S(=O)(=O)(O)O>CO.ClCCl.[Pt]>[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:19]2[C:9]3=[CH:10][CH2:11][C@@:12]4([CH3:18])[C@H:16]([C@@H:8]3[CH2:7][CH2:6][C:5]=2[CH:4]=1)[CH2:15][CH2:14][C:13]4=[O:17]

Komponenten

7

Edukt 3

HCID 1118Sulfuric AcidHCID 92895(+)-Estrone 3-methyl etherHCID 517045Sodium Acetate

Produkt 1

HCID 128111663-Methoxyestra-1,3,5(10),9(11)-tetraen-17-oneAusbeute 83,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23939PlatinumKatalysatorHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 3.0 grams of 3-methoxy-13β-methylgona-1,3,5(10)-trien-17-one and 0.66 gram of sodium acetate in 60 milliliters of methanol and 20 milliliters of dichloromethane was electroyzed between the same platinum electrodes as specified in Example 1 while a potential of 1.7 volts (measured at the anode against a standard saturated calomel electrode) was maintained between the electrodes. At the completion of the electrolysis, which was established by thin-layer chromatography, the solution was made slightly acid by adding sulfuric acid thereto and it was allowed to stand at room temperature for a period between 20 and 30 minutes. Thereafter the dichloromethane was distilled and the product was crystallized from the remaining methanolic solution. In this manner, 2.5 grams of 3-methoxy-13β-methylgona-1,3,5(10),9(11)-tetraen- 17-one having a melting point of 142°- 145° C. was obtained.

Aufarbeitung

  1. temperaturewas maintained between the electrodes
  2. waitto stand at room temperature for a period between 20 and 30 minutes
  3. distillationThereafter the dichloromethane was distilled
  4. customthe product was crystallized from the remaining methanolic solution

Quellen und Nachweise

ORD-Eintrag
ord-db87d04916e1459f81bcb5a34c679656
Quelldatensatz
uspto-grants-1977_06
Patentnummer
US04029648

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