Pyrazole → 4-(1H-Pyrazol-1-yl)benzaldehyde

HRID 1867239Notes

Reaction equation

HRID 1867239 reaction equation
N1C=CC=CC=1.[CH:7]([C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1)=[O:8].[NH:18]1[CH:22]=[CH:21][CH:20]=[N:19]1>O1CCOCC1.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH:7]([C:9]1[CH:14]=[CH:13][C:12]([N:18]2[CH:22]=[CH:21][CH:20]=[N:19]2)=[CH:11][CH:10]=1)=[O:8]

Participants

6

Reactant 3

HCID 1048PyrazoleHCID 1049PyridineHCID 5910734-Formylphenylboronic Acid

Product 1

HCID 27764774-(1H-Pyrazol-1-yl)benzaldehydeYield 66.9%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

Copper acetate (91 mg, 0.5 mmol), pyridine (53 mg, 0.67 mmol) and active Molecular Sieve 4A (250 mg) were added to a solution of 4-formylphenylboronic acid (100 mg, 0.67 mmol) and pyrazole (16 mg, 0.33 mmol) in 1,4-dioxane (4 ml), and they were stirred at room temperature for 72 hours. The reaction mixture was filtered through Celite, and the obtained filtrate was concentrated and then purified by the silica gel TLC chromatography to obtain 1-(4-formylphenyl)pyrazole (yield: 38 mg, 66%) in the form of a white powder.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe obtained filtrate was concentrated
  3. custompurified by the silica gel TLC chromatography

Sources & evidence

ORD record
ord-e9a4a07c76424f88a6b0f4fb96006c78
Source dataset
uspto-grants-2009_12
Patent number
US07632830B2

Reaction notes

Loading…