Sodium Chloride → Ethyl (4-formyl-1H-pyrazol-1-yl)acetate

HRID 1171755Notes

Reaction equation

HRID 1171755 reaction equation
[NH:1]1[CH:5]=[C:4]([CH:6]=[O:7])[CH:3]=[N:2]1.Br[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].N12CCCN=C1CCCCC2.[Cl-].[Na+]>ClCCl>[CH2:13]([O:12][C:10](=[O:11])[CH2:9][N:1]1[CH:5]=[C:4]([CH:6]=[O:7])[CH:3]=[N:2]1)[CH3:14]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 7748Ethyl bromoacetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 51306731H-pyrazole-4-carbaldehyde

Product 1

HCID 53491200Ethyl (4-formyl-1H-pyrazol-1-yl)acetateYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1H-pyrazole-4-carbaldehyde (5.5 g) and ethyl bromoacetate (19.0 g) in dichloromethane (150 ml), was added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (10 ml) at 0° C. The resulting mixture was stirred at room temperature for 30 minutes, and the reaction was stopped by addition of a saturated aqueous sodium chloride solution. The products were extracted with ethyl acetate, and the extract was dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo, and the residue was purified by chromatography on silica gel using a mixture of hexane and ethyl acetate (1:3) as the eluent to afford the title compound as a colourless oil (8.09 g, yield: 78%).

Workup

  1. extractionThe products were extracted with ethyl acetate
  2. dry with materialthe extract was dried over anhydrous sodium sulfate
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was purified by chromatography on silica gel using
  5. additiona mixture of hexane and ethyl acetate (1:3) as the eluent

Sources & evidence

ORD record
ord-4c3294accec040ef917e4b2f2e23d813
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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