Sodium Cyanide → 2-(3-(2,6-Dimethylbenzyloxy)-4-methoxyphenyl)acetonitrile

HRID 1958845Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1958845
[CH3:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[CH2:9][C:10]1NN=N[N:11]=1.[C-]#N.[Na+]>CN(C=O)C.CCOC(C)=O>[CH3:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:2]([CH3:1])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:9][C:10]#[N:11])[CH:15]=[CH:16][C:17]=1[O:18][CH3:19]

Komponenten

5

Edukt 2

HCID 8929Sodium CyanideHCID 1784899435-(3-(2,6-Dimethylbenzyloxy)-4-methoxybenzyl)-1H-tetrazole

Produkt 1

HCID 669590872-(3-(2,6-Dimethylbenzyloxy)-4-methoxyphenyl)acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The solution of 2-((5-(bromomethyl)-2-methoxyphenoxy)methyl)-1,3-dimethylbenzene (Step D, 3.28 g, 9.7 mmol) and NaCN (0.624 g, 12.7 mmol) in dry DMF (20 ml) was heated at 120° C. for 2.5 hours then cooled and diluted with EtOAc (50 ml). The organic layer was washed with water (30 ml), brine, dried over Na2SO2, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex:ethyl acetate 2:1) 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 Na2SO2
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography on a silica gel column (hex:ethyl acetate 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-a9d598ec38564ea59d2abc3510900e93
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410154B2

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