3-Pyridinecarboxaldehyde → (3,4-Dimethoxyphenyl)(pyridin-3-yl)methanol

HRID 928756Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 928756
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([Mg]Br)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[OH:20])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Komponenten

4

Edukt 2

HCID 103713-PyridinecarboxaldehydeHCID 178491916HCID 178491916, Verbindung

Produkt 1

HCID 13475606(3,4-Dimethoxyphenyl)(pyridin-3-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(3,4-dimethoxyphenyl)magnesium bromide (0.5 M in THF, 9.5 mL, 4.75 mmol) was added dropwise by syringe to a solution of nicotinaldehyde (0.88 mL, 9.37 mmol) in dry THF (20 mL) at 0° C. The reaction mixture was stirred for 30 minutes at 0° C., then quenched with saturated aqueous ammonium chloride solution. The mixture was partitioned between water and ethyl acetate. The separated aqueous phase was further extracted with ethyl acetate. The organic phase was dried (Na2SO4), filtered, and concentrated. The crude product was purified by flash column chromatography (silica gel, 0-60% EtOAc-hexanes) to provide the title compound as a brown oil.

Aufarbeitung

  1. customquenched with saturated aqueous ammonium chloride solution
  2. customThe mixture was partitioned between water and ethyl acetate
  3. extractionThe separated aqueous phase was further extracted with ethyl acetate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash column chromatography (silica gel, 0-60% EtOAc-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-f20538a36b8d4b4e8fe1dc1b9434b75f
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290476B2

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