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Water → HCID 54302982, Verbindung

HRID 1415851
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1415851
[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].[CH3:27][Al](C)C.O>O1CCOCC1.C1(C)C=CC=CC=1.[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]([CH3:27])[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 3

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

Produkt 1

HCID 54302982HCID 54302982, VerbindungAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24593copper(I) bromideKatalysator
HCID 1140
Toluene
Lösungsmittel
HCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °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. 9.4 ml (11 mmol) of a 10% solution of trimethyl aluminum in toluene is added to the reaction at room temperature under nitrogen atmosphere and, after completion of the addition, stirred for 10 minutes at 20° 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 filtered off with dioxane is 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, 1.12 g of 3-acetoxy-16α-methyl-pregn-5-en-20-one (30% of theory) 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 filtered off with dioxane
  5. washis washed 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

Quellen und Nachweise

ORD-Eintrag
ord-e9e1e785a23c4a8d8209e44422037d65
Quelldatensatz
uspto-grants-1999_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05908944

Notizen zur Reaktion

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