Sodium Cyanide → 2-(3-(2,6-Dimethylbenzyloxy)-2-methylphenyl)acetonitrile

HRID 337266Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 337266
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH2:10][C:11]2[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:18])[C:4]=1[CH3:19].[C-:20]#[N:21].[Na+]>CN(C=O)C.CCOC(C)=O>[CH3:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([CH3:17])[C:11]=1[CH2:10][O:9][C:5]1[C:4]([CH3:19])=[C:3]([CH2:2][C:20]#[N:21])[CH:8]=[CH:7][CH:6]=1

Komponenten

5

Edukt 2

HCID 8929Sodium CyanideHCID 669593551-(Bromomethyl)-3-(2,6-dimethylbenzyloxy)-2-methylbenzene

Produkt 1

HCID 669591112-(3-(2,6-Dimethylbenzyloxy)-2-methylphenyl)acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The solution of 1-(bromomethyl)-3-(2,6-dimethylbenzyloxy)-2-methylbenzene (Step D, 4.28 g, 13.41 mmol) and NaCN (0.789 g, 16.10 mmol) in dry DMF (20 ml) was heated at 120° C. for 3 hours then cooled and diluted with EtOAc (50 ml). The organic layer was washed with water (30 ml), brine, dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex: ethyl acetate 4:1) to give the title compound.

Aufarbeitung

  1. temperaturethen cooled
  2. washThe organic layer was washed with water (30 ml), brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography on a silica gel column (hex: ethyl acetate 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-4d8f6f5382304f9c9675d6f40d5824b6
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889724B2

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