3-(3-Formyl-pyridin-4-yl)-benzonitrile → 3-{3-[(4-Tert-butyl-phenyl)-hydroxy-methyl]-pyridin-4-yl)-benzonitrile

HRID 1712084Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1712084
[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].[C:17]([C:21]1[CH:26]=[CH:25][C:24]([Mg]Br)=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18]>C1COCC1>[C:17]([C:21]1[CH:26]=[CH:25][C:24]([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:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18]

Komponenten

4

Edukt 2

HCID 592052083-(3-Formyl-pyridin-4-yl)-benzonitrileHCID 178440986HCID 178440986, Verbindung

Produkt 1

HCID 592052063-{3-[(4-Tert-butyl-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 2.0 M 4-tert-butylphenylmagnesium bromide in THF (0.15 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-tert-butyl-phenyl)-hydroxy-methyl]-pyridin-4-yl}-benzonitrile as a colorless oil.

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-1ae69ec4fec6484797c25ed978457d99
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790895B2

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