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

HRID 1958858Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1958858
[CH3:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([CH3:18])=[C:8]([CH:15]=[CH:16][CH:17]=1)[CH2:9][C:10]1NN=N[N:11]=1.[C-]#N.[Na+]>CN(C=O)C.CCOC(C)=O>[CH3:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([CH3:18])=[C:8]([CH2:9][C:10]#[N:11])[CH:15]=[CH:16][CH:17]=1

Komponenten

5

Edukt 2

HCID 8929Sodium CyanideHCID 178424789HCID 178424789, Verbindung

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-1bda22fd116c43f9a54b19c7c6366bf0
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410154B2

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