HCID 22477758, compound → HCID 22477919, compound

HRID 2064579Notes

Reaction equation

HRID 2064579 reaction equation
[CH2:1]([N:8]1[C:12]([CH2:13][OH:14])=[CH:11][C:10]([O:15][CH2:16][CH3:17])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH2:1]([N:8]1[C:12]([CH:13]=[O:14])=[CH:11][C:10]([O:15][CH2:16][CH3:17])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 22477758HCID 22477758, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 22477919HCID 22477919, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4 Å molecular sieves are added to a solution of 45.7 mg of (2-benzyl-5-ethoxy-2H-pyrazol-3-yl)methanol in 0.5 ml of dichloromethane, followed by addition of 43.1 mg of pyridinium chlorochromate. After 20 hours at a temperature in the region of 20° C., the reaction mixture is filtered through Celite. The insoluble material formed is rinsed with ethyl acetate and then with dichloromethane. The filtrate is washed with water. After separation of the phases by settling, the aqueous phase is re-extracted with dichloromethane. The organic phases are combined, dried over magnesium sulphate, filtered and then concentrated under reduced pressure. 21.6 mg of 2-benzyl-5-ethoxy-2H-pyrazole-3-carboxaldehyde are thus obtained in the form of a brown lacquer, the characteristics of which are as follows:

Workup

  1. filtrationthe reaction mixture is filtered through Celite
  2. customThe insoluble material formed
  3. washis rinsed with ethyl acetate
  4. washThe filtrate is washed with water
  5. customAfter separation of the phases
  6. extractionthe aqueous phase is re-extracted with dichloromethane
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bb2273dcc4874c4ea6bb482d4ece0869
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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