Water → 4-[3-methyl-1-(2-pyridyl)-1H-pyrazol-4-ylmethoxy]benzaldehyde

HRID 349924Notes

Reaction equation

HRID 349924 reaction equation
[H-].[Na+].[CH3:3][C:4]1[C:8]([CH2:9][OH:10])=[CH:7][N:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:5]=1.F[C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=1.O>CN(C)C=O>[CH3:3][C:4]1[C:8]([CH2:9][O:10][C:18]2[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=2)=[CH:7][N:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 23076503[3-Methyl-1-(pyridin-2-yl)-1H-pyrazol-4-yl]methanol

Product 1

HCID 867604184-[3-methyl-1-(2-pyridyl)-1H-pyrazol-4-ylmethoxy]benzaldehydeYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60%, oily, 0.80 g) was added to a solution of [3-methyl-1-(2-pyridyl)-1H-pyrazol-4-yl]methanol (3.20 g) in N,N-dimethylformamide (50 ml) at 0° C., and the mixture was stirred at room temperature for one hour. 4-fluorobenzaldehyde (2 ml) was added to the reaction mixture, and the mixture was stirred overnight at 50° C. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and then concentrated. The residue was subjected to silica gel column chromatography, and 4-[3-methyl-1-(2-pyridyl)-1H-pyrazol-4-ylmethoxy]benzaldehyde (4.26 g, yield: 86%) was obtained as colorless crystals from the fraction eluted with ethyl acetate-hexane (1:2, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 84–85° C.

Workup

  1. stirringthe mixture was stirred overnight at 50° C
  2. extractionwas extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-89a4efc031f442a183adb41a574dc0ee
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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