Dichloromethane → (3beta)-3-[(1-Ethoxyethyl)oxy]pregn-5-en-20-one

HRID 1385614

Reaktionsgleichung

Reaktionsgleichung von HRID 1385614
[OH:1][C@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:23])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1.C(N([CH2:29][CH3:30])CC)C.[C:31](=[O:34])([O-])O.[Na+].Cl[CH2:37]Cl>C(OCC)=C>[CH2:31]([O:34][CH:29]([O:1][C@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:23])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1)[CH3:30])[CH3:37]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 8955PregnenoloneHCID 516892Sodium Bicarbonate

Produkt 1

HCID 54547839(3beta)-3-[(1-Ethoxyethyl)oxy]pregn-5-en-20-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8023Ethyl vinyl etherLösungsmittel

Versuchsvorschrift

—Pyridium p-toluenesulfonate (6.32 g) was added to a solution of (3β)-3-hydroxypregn-5-en-20-one (1; 100 g) in dichloromethane (600 ml) and ethyl vinyl ether (200 ml). After stirring of the reaction mixture for 1 h at room temperature triethylamine (20 ml) was added, whereupon the mixture was poured into a saturated aqueous solution of sodium hydrogen carbonate (1 l). The product was extracted into dichloromethane; the combined organic phases were washed with brine, dried over sodium sulfate, and concentrated under reduced pressure to give (3β)-3-[(1-ethoxyethyl)oxy]pregn-5-en-20-one (2; 125.6 g), which was used in the following step without further purification.

Aufarbeitung

  1. additionwas added, whereupon the mixture
  2. extractionThe product was extracted into dichloromethane
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-54bf1e1641c34d278e4fcfa6bb5d015f
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06262282B1

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