Estradiol → Estradiol 3-methyl ether

HRID 649743

Reaktionsgleichung

Reaktionsgleichung von HRID 649743
[CH3:1][C@@:2]12[C@@H:18]([OH:19])[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:20])=[CH:10][C:11]=3[CH2:12][CH2:13]1)[CH2:4][CH2:3]2.[OH-].[Na+].[CH3:23]OS([O-])(=O)=O>C(O)C.O>[CH3:1][C@@:2]12[C@@H:18]([OH:19])[CH2:17][CH2:16][C@H:15]1[C@@H:14]1[CH2:13][CH2:12][C:11]3[CH:10]=[C:9]([O:20][CH3:23])[CH:8]=[CH:7][C:6]=3[C@H:5]1[CH2:4][CH2:3]2

Komponenten

6

Edukt 3

HCID 5757EstradiolHCID 14798Sodium HydroxideHCID 4694097Methyl sulfate(1-)

Produkt 1

HCID 246206Estradiol 3-methyl ether

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of estradiol (10.0 g, 36.7 mmol) in ethanol (100 ml) at reflux was added NaOH (100 mmol) in water (10 ml) followed by the dropwise addition of methylsulfate (Me2SO4) (100 mmol). Neutralization with 10% HCl, subsequent concentration of the mixture followed by filtration through silica gel with ethyl ether, afforded 3-methoxyestradiol as white needles. Dissolving metal reduction of 3-methoxyestradiol was carried out via the methods described by Wilds and affording the known dihydroestradiene derivative as a white solid. (See Feiser, L. F., Feiser, M. “Reagents for Organic Synthesis”, John Wiley and Sons, Inc., New York, 1967, pp. v, 583-4, 622-3.)

Aufarbeitung

  1. concentrationNeutralization with 10% HCl, subsequent concentration of the mixture
  2. filtrationfollowed by filtration through silica gel with ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-d1284641609c41179e0bd55d32fa2f5e
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06271220B1

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