4-Methylpyrazole → 4-(4-Methyl-1H-pyrazol-1-yl)benzaldehyde

HRID 1166082Notes

Reaction equation

HRID 1166082 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.[H-].[Na+].F[C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=1>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[N:4][N:5]([C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 34064-MethylpyrazoleHCID 24758Sodium hydrideHCID 680234-Fluorobenzaldehyde

Product 1

HCID 226307814-(4-Methyl-1H-pyrazol-1-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 4-methylpyrazole (1.98 g, 24.11 mmol) in DMF (8 mL) was added to sodium hydride (60% in oil, 0.97 g, 24.25 mmol) in DMF (6 mL) and the resulting mixture was stirred 2 h at RT. 4-Fluorobenzaldehyde (1.26 g, 7.45 mmol) was added dropwise and the resulting mixture heated to 80° C. for 3 h. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 4:1 hexane/ethyl acetate) followed by recrystallization from hexane yielded the title compound. MS 187 (M+H)+.

Workup

  1. temperaturethe resulting mixture heated to 80° C. for 3 h
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customPurification by chromatography (SiO2, 4:1 hexane/ethyl acetate)
  7. customfollowed by recrystallization from hexane

Sources & evidence

ORD record
ord-803cae93105d40b0a72672178e2e3c5d
Source dataset
uspto-grants-2003_09
Patent number
US06613747B2

Reaction notes

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