Sodium Chloride → 1-(4-Methoxy-dibenzofuran-1-yl)-4-oxo-cyclohexane carbonitrile

HRID 2383976

Reaktionsgleichung

Reaktionsgleichung von HRID 2383976
COC([CH:5]1[CH2:10][C:9]([C:26]#[N:27])([C:11]2[C:19]3[C:18]4[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=4[O:16][C:15]=3[C:14]([O:24][CH3:25])=[CH:13][CH:12]=2)[CH2:8][CH2:7][C:6]1=[O:28])=O.[Cl-].[Na+]>CS(C)=O.O>[CH3:25][O:24][C:14]1[C:15]2[O:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[C:19]=2[C:11]([C:9]2([C:26]#[N:27])[CH2:8][CH2:7][C:6](=[O:28])[CH2:5][CH2:10]2)=[CH:12][CH:13]=1

Komponenten

5

Edukt 2

HCID 5234Sodium ChlorideHCID 247555955-Cyano-5-(4-methoxy-dibenzofuran-1-yl)-2-oxo-cyclohexane carboxylic acid methyl ester

Produkt 1

HCID 248041271-(4-Methoxy-dibenzofuran-1-yl)-4-oxo-cyclohexane carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

To a solution of 5-cyano-5-(4-methoxy-dibenzofuran-1-yl)-2-oxo-cyclohexane carboxylic acid methyl ester obtained in example 1 (7 g, 0.0185 mol) in DMSO (140 ml) and water (9 ml) was added sodium chloride (7 g, 0.119 mol) at room temperature. The reaction mass was heated to 130-140° C. for 5 hrs. Once the product is formed, the reaction mass was quenched with water and extracted with ethyl acetate. The organic layer was dried with sodium sulfate and concentrated under vacuum. 1-(4-methoxy-dibenzofuran-1-yl)-4-oxo-cyclohexane carbonitrile was isolated by column chromatography. Yield 4.2 g (71%)

Aufarbeitung

  1. customOnce the product is formed
  2. customthe reaction mass was quenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c7d7fbdaa2f94d4e93cbd2f991291e96
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263648B2

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