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Water → HCID 67557649, Verbindung

HRID 1415853
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1415853
[C:1]([O:4][CH:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@H:11]3[CH2:12][CH:13]=[C:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1)(=[O:3])[CH3:2].C[Al](C)C.O.O1CCO[CH2:34][CH2:33]1>CCCCCC.[Cu]Br>[C:1]([O:4][CH:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@H:11]3[CH2:12][C@@H:13]([CH2:33][CH3:34])[C@@H:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1)(=[O:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 312751,4-Dioxane2×HCID 109043983-Hydroxypregna-5,16-dien-20-one 3-acetateHCID 16682925Trimethylaluminum

Produkt 1

HCID 67557649HCID 67557649, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24593
copper(I) bromide
Katalysator
HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
22 °C

Versuchsvorschrift

3.56 g (10 mmol) of 3-acetoxy-pregna-5,16-dien-20-one is dissolved in 20 ml of dioxane at 20° C. and mixed with 143.3 g (1 mmol) of copper(I) bromide. 11 ml (11 mmol) of a 1 molar solution of trimethyl aluminum in hexane is added to the reaction at room temperature under nitrogen atmosphere and, after completion of the addition, stirred for 3 hours more at 22° C. For hydrolysis of the reaction solution, 1 ml of water dissolved in 5 ml of dioxane is carefully added to the reaction. It is stirred for 10 minutes more and the inorganic precipitate is filtered off with dioxane and washed again. The dioxane solution is concentrated by evaporation on a rotary evaporator and the residue is chromatographed on silica gel with ethyl acetate/hexane as eluent. After concentration by evaporation of the fractions, 1.72 g of 3-acetoxy-16α-ethyl-pregn-5-en-20-one (45% of theory) of a melting point of 114.9° C. is obtained.

Aufarbeitung

  1. additionafter completion of the addition
  2. additionis carefully added to the reaction
  3. stirringIt is stirred for 10 minutes more
  4. filtrationthe inorganic precipitate is filtered off with dioxane
  5. washwashed again
  6. concentrationThe dioxane solution is concentrated by evaporation on a rotary evaporator
  7. customthe residue is chromatographed on silica gel with ethyl acetate/hexane as eluent
  8. concentrationAfter concentration
  9. customby evaporation of the fractions, 1.72 g of 3-acetoxy-16α-ethyl-pregn-5-en-20-one (45% of theory) of a melting point of 114.9° C.
  10. customis obtained

Quellen und Nachweise

ORD-Eintrag
ord-8bed8918a56743c38e11d471ec4cb389
Quelldatensatz
uspto-grants-1999_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05908944

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