Chloroacetonitrile → 2-[(3,4-Dichloro-6,7,8,8a,9,10-hexahydro-6-oxo-8a-propyl-2-phenanthrenyl)oxy]acetonitrile

HRID 867991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 867991
[Cl:1][C:2]1[C:3]([OH:21])=[CH:4][C:5]2[CH2:6][CH2:7][C:8]3([CH2:18][CH2:19][CH3:20])[C:13]([C:14]=2[C:15]=1[Cl:16])=[CH:12][C:11](=[O:17])[CH2:10][CH2:9]3.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:29][C:30]#[N:31]>CN(C)C=O>[Cl:1][C:2]1[C:3]([O:21][CH2:29][C:30]#[N:31])=[CH:4][C:5]2[CH2:6][CH2:7][C:8]3([CH2:18][CH2:19][CH3:20])[C:13]([C:14]=2[C:15]=1[Cl:16])=[CH:12][C:11](=[O:17])[CH2:10][CH2:9]3

Komponenten

5

Edukt 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 212895743,4-Dichloro-6,7,8,8a,9,10-hexahydro-2-hydroxy-6-oxo-8a-propylphenanthrene

Produkt 1

HCID 212895702-[(3,4-Dichloro-6,7,8,8a,9,10-hexahydro-6-oxo-8a-propyl-2-phenanthrenyl)oxy]acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A stirred mixture of 3,4-dichloro-6,7,8,8a,9,10-hexahydro-2-hydroxy-6-oxo-8a-propylphenanthrene (0.4 g, 1.22 mmole), potassium carbonate (0.2 g, 1.45 mmole) and chloroacetonitrile (160 μl, 1.78 mmole) in dimethylformamide (7 ml) is heated at 65° C. for 2 hours, poured into ice water, extracted with ether, washed with water, brine, dried over MgSO4 and evaporated in vacuo. Trituration of the residual oil with butyl chloride give 2-[(3,4-dichloro-6,7,8,8a,9,10-hexahydro-6-oxo-8a-propyl-2-phenanthrenyl)oxy]acetonitrile which is removed by filtration, and dried.

Aufarbeitung

  1. extractionextracted with ether
  2. washwashed with water, brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-15ae3c2fb8f941b686a7c04f9561958e
Quelldatensatz
uspto-grants-1988_10
Patentnummer
US04777281

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