Water → 7alpha-(5-Chloropentyl)-3-hydroxy-estra-1,3,5(10)-trien-17-one

HRID 650352Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 650352
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[C@H:18]([CH2:19][CH2:20][C:21](=[O:25])[CH:22]=2)[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][CH2:16]2)([CH3:14])[C:12](=[O:26])[CH2:11][CH2:10]1.[Br-].[Li+].O.C(=O)(O)[O-].[Na+]>C(#N)C.[Cu]Br.C(OCC)(=O)C>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[CH:22]=[C:21]([OH:25])[CH:20]=[CH:19][C:18]=2[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][CH2:16]2)([CH3:14])[C:12](=[O:26])[CH2:11][CH2:10]1

Komponenten

8

Edukt 4

HCID 962WaterHCID 82050Lithium BromideHCID 516892Sodium BicarbonateHCID 571565697alpha-(5-Chloropentyl)-estr-4-ene-3,17-dione

Produkt 1

HCID 229418087alpha-(5-Chloropentyl)-3-hydroxy-estra-1,3,5(10)-trien-17-oneAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24593copper(I) bromideKatalysatorHCID 6342AcetonitrileLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

18.96 g of 7α-(5-chloropentyl)-estr-4-ene-3,17-dione is dissolved in 350 ml of anhydrous acetonitrile and mixed under inert gas at 80° C. with a solution of 4.36 g of lithium bromide and 22.5 g of copper(I) bromide in 390 ml of anhydrous acetonitrile. It is stirred for 5 more minutes, the mixture is cooled in an ice bath and mixed with water and ethyl acetate. The organic phase is shaken out with saturated sodium bicarbonate solution, the aqueous phase with ethyl acetate, the combined organic phases with saturated common salt solution, dried with sodium sulfate and concentrated by evaporation in a vacuum. The raw yield of 19.1 g is chromatographed on silica gel in hexane and ethyl acetate, whereby 10.0 g of oily 7α-(5-chloropentyl)-3-hydroxy-estra-1,3,5(10)-trien-17-one is obtained, which can be crystallized from hexane/dichloromethane.

Aufarbeitung

  1. temperaturethe mixture is cooled in an ice bath
  2. dry with materialthe aqueous phase with ethyl acetate, the combined organic phases with saturated common salt solution, dried with sodium sulfate
  3. concentrationconcentrated by evaporation in a vacuum
  4. customThe raw yield of 19.1 g is chromatographed on silica gel in hexane and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-be02c070916f4c7bbf6e3121cc0fb5bb
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06271403B1

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