Pyrazole → 3-(1h-pyrazol-1-yl)benzaldehyde

HRID 2416438Notes

Reaction equation

HRID 2416438 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1)=[O:2].[NH:12]1[CH:16]=[CH:15][CH:14]=[N:13]1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[N:12]1([C:5]2[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=2)[CH:1]=[O:2])[CH:16]=[CH:15][CH:14]=[N:13]1

Participants

6

Reactant 3

HCID 1048PyrazoleHCID 1049PyridineHCID 27343563-Formylphenylboronic acid

Product 1

HCID 71723093-(1h-pyrazol-1-yl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-formylphenylboronic acid (2.00 g, 13.34 mmol), pyrazole (0.46 g, 6.67 mmol), copper(II) acetate (1.82 g, 10.01 mmol), pyridine (1.10 mL, 13.34 mmol), and powdered 4A molecular sieves (2.5 g) in dichloromethane (20 mL) was stirred under an air atmosphere for 24 h. The mixture was then filtered through Celite, the filtered solids were washed with methanol, and the combined filtrate was concentrated. Purification by chromatography (SiO2, 3:1 hexane/ethyl acetate) yielded the title compound. MS 173 (M+H)+.

Workup

  1. filtrationThe mixture was then filtered through Celite
  2. washthe filtered solids were washed with methanol
  3. concentrationthe combined filtrate was concentrated
  4. customPurification by chromatography (SiO2, 3:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5ac8226e490c4ac3867bc8947627b803
Source dataset
uspto-grants-2004_11
Patent number
US06825170B2

Reaction notes

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