Pyrazole → 3-Methoxy-4-(1H-pyrazol-1-YL)benzaldehyde

HRID 992923Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 992923
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11].[NH:12]1[CH:16]=[CH:15][CH:14]=[N:13]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH3:11][O:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[N:12]1[CH:16]=[CH:15][CH:14]=[N:13]1)[CH:6]=[O:7]

Komponenten

6

Edukt 3

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 27373584-Fluoro-3-methoxybenzaldehyde

Produkt 1

HCID 226310043-Methoxy-4-(1H-pyrazol-1-YL)benzaldehydeAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 4-fluoro-3-methoxybenzaldehyde (2.00 g, 12.98 mmol), pyrazole (1.32 g, 19.39 mmol), and powdered K2CO3 (2.68 g, 19.39 mmol) in DMF (20 mL) was heated to 120° C. for 20 h. The cooled reaction mixture was diluted with ethyl acetate (200 mL), washed with water (3×200 mL), dried (Na2SO4), and concentrated. Purification by chromatography (SiO2, 4:1 hexane/ethyl acetate) yielded 1.52 g (58%) of the title compound as a yellow oil. MS 203 (M+H)+.

Aufarbeitung

  1. customThe cooled reaction mixture
  2. washwashed with water (3×200 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification by chromatography (SiO2, 4:1 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-83e91c21a6ec46969a44efb0549468e7
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06472372B1

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