3-(3-Formyl-pyridin-4-yl)-benzonitrile → 3-(3-[(4-Chloro-phenyl)-hydroxy-methyl]-pyridin-4-yl}-benzonitrile

HRID 1712083Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1712083
[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].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([Mg]Br)=[CH:20][CH:19]=1>C1COCC1>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH:1]([OH:2])[C:3]2[CH:4]=[N:5][CH:6]=[CH:7][C:8]=2[C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])=[CH:20][CH:19]=1

Komponenten

4

Edukt 2

HCID 592052083-(3-Formyl-pyridin-4-yl)-benzonitrileHCID 178478191HCID 178478191, Verbindung

Produkt 1

HCID 592051933-(3-[(4-Chloro-phenyl)-hydroxy-methyl]-pyridin-4-yl}-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 3-(3-formyl-pyridin-4-yl)-benzonitrile (30 mg, 0.15 mmol) in THF (1.5 mL) at −78° C. was added 0.5 M 4-chlorophenylmagnesium bromide in THF (0.6 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-[(4-chloro-phenyl)-hydroxy-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-82ccb464e77c442790cc21c4823e4977
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790895B2

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