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

HRID 1166081Notes

Reaction equation

HRID 1166081 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 MeOH, 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 MeOH
  3. concentrationthe combined filtrate was concentrated
  4. customPurification by chromatography (SiO2, 3:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-8ab7f307366b4b16b101de06755c83cd
Source dataset
uspto-grants-2003_09
Patent number
US06613747B2

Reaction notes

Loading…