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Hydrogen Peroxide → 20-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxypregna-4,6-dien-3-one

HRID 1708744
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1708744
[OH-].[Na+].OO.[CH3:5][C:6]1([CH3:34])[CH2:11][O:10][CH:9]([CH:12]([C@@H:14]2[C@:31]3([CH3:32])[C@H:17]([C@H:18]4[C@H:28]([CH2:29][CH2:30]3)[C@:26]3([CH3:27])[C:21](=[CH:22][C:23](=[O:33])[CH:24]=[CH:25]3)[CH:20]=[CH:19]4)[CH2:16][CH2:15]2)[CH3:13])[O:8][CH2:7]1.C(OCC)(=[O:37])C.CCCCCC>CO.O>[CH3:34][C:6]1([CH3:5])[CH2:7][O:8][CH:9]([CH:12]([C@@H:14]2[C@:31]3([CH3:32])[C@H:17]([C@H:18]4[C@H:28]([CH2:29][CH2:30]3)[C@:26]3([CH3:27])[C:21](=[CH:22][C:23](=[O:33])[C@@H:24]5[O:37][C@@H:25]53)[CH:20]=[CH:19]4)[CH2:16][CH2:15]2)[CH3:13])[O:10][CH2:11]1
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Komponenten

7

Edukt 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 21226206Ethyl acetate hexaneHCID 2284393220-(5,5-Dimethyl-1,3-dioxan-2-yl)pregna-1,4,6-trien-3-one

Produkt 1

HCID 8674579720-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxypregna-4,6-dien-3-oneAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A 10 weight % solution of sodium hydroxide in methanol (1.16 ml) and 6.36 ml of a 30 weight % solution of hydrogen peroxide in water (containing 62.3 mmoles of hydrogen peroxide) were added to a solution of 4.66 g (11.3 mmoles) of 20-(5,5-dimethyl-1,3-dioxan-2-yl)pregna-1,4,6-trien-3-one in 150 ml of methanol and the mixture was stirred at room temperature for 16 hours. The reaction mixture thus obtained was diluted with water and after the methanol was partially distilled off under reduced pressure at room temperature, the residue was extracted with ether. The extract was washed successively with aqueous potassium iodide solution and aqueous sodium chloride solution and the organic layer was dried over magnesium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel chromatography (eluent: ethyl acetate/hexane=1: 10, v/v) to recover 3.72 g of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxypregna-4,6-dien-3-one (yield: 77%).

Aufarbeitung

  1. customThe reaction mixture thus obtained
  2. distillationafter the methanol was partially distilled off under reduced pressure at room temperature
  3. extractionthe residue was extracted with ether
  4. washThe extract was washed successively with aqueous potassium iodide solution and aqueous sodium chloride solution
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. distillationThe solvent was then distilled off under reduced pressure
  7. customthe residue was purified by silica gel chromatography (eluent

Quellen und Nachweise

ORD-Eintrag
ord-657177ed05b94261b5aecf968c22db28
Quelldatensatz
uspto-grants-1994_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05359055

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