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

HRID 1166083Notes

Reaction equation

HRID 1166083 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

HCID 226310043-Methoxy-4-(1H-pyrazol-1-yl)benzaldehydeYield 58%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-6c76426c9a6446458db9c6b2855a2f45
Source dataset
uspto-grants-2003_09
Patent number
US06613747B2

Reaction notes

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