3-(3-Formyl-pyridin-4-yl)-benzonitrile → 3-[3-[Hydroxy-(2,5-dimethoxy-phenyl)-methyl]-pyridin-4-yl)-benzonitrile

HRID 2242130Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2242130
[CH:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[C:12]#[N:13])=[O:2].[O:17]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=1[Mg]Br)[CH3:18]>C1COCC1>[OH:2][CH:1]([C:23]1[CH:24]=[C:19]([O:17][CH3:18])[CH:20]=[CH:21][C:22]=1[O:25][CH3:26])[C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[C:12]#[N:13]

Komponenten

4

Edukt 2

HCID 592052083-(3-Formyl-pyridin-4-yl)-benzonitrileHCID 178492591HCID 178492591, Verbindung

Produkt 1

HCID 684988763-[3-[Hydroxy-(2,5-dimethoxy-phenyl)-methyl]-pyridin-4-yl)-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 3-(3-formyl-pyridin-4-yl)-benzonitrile (15 mg, 0.075 mmol) in THF (1 mL) at −78° C. was added 0.5 M 2,5-dimethoxylphenylmagnesium bromide in THF (0.3 mL). The reaction mixture was quenched with ammonium chloride and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated, and the residue purified by flash chromatography eluted with 5% methanol in dichloromethane to yield 3-{3-[hydroxy-(2,5-dimethoxy-phenyl)-methyl]-pyridin-4-yl}-benzonitrile as white crystals.

Aufarbeitung

  1. customThe reaction mixture was quenched with ammonium chloride
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue purified by flash chromatography
  6. washeluted with 5% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-b60c5d60ae344e87a1494e3083521ea3
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07671065B2

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