Dimethylformamide → benzyl 4-[4-(3-ethoxy-3-oxo-1-propyl)-3-phenyl-1H-pyrazole-1-ylmethyl]benzoate

HRID 349926Notes

Reaction equation

HRID 349926 reaction equation
[H-].[Na+].[C:3]1([C:9]2[C:13]([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][NH:11][N:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[CH2:22][C:23]1[CH:38]=[CH:37][C:26]([C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])=[CH:25][CH:24]=1.CN(C)C=O>O>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][CH2:14][C:13]1[C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[N:10][N:11]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:27]([O:29][CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[O:28])=[CH:37][CH:38]=2)[CH:12]=1)[CH3:20]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 12194612Benzyl 4-chloromethylbenzoateHCID 178471160HCID 178471160, compound

Product 1

HCID 23024857benzyl 4-[4-(3-ethoxy-3-oxo-1-propyl)-3-phenyl-1H-pyrazole-1-ylmethyl]benzoateYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60%, oily, 180 mg) was added to a mixture of ethyl 3-(3-phenyl-1H-pyrazol-4-yl)propionate (1.00 g), benzyl 4-chloromethylbenzoate (1.17 g), and N,N-dimethylformamide (10 ml) at 0° C., and the mixture was stirred for 2.5 days at room temperature. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and then concentrated. The residue was subjected to silica gel column chromatography, and benzyl 4-[4-(3-ethoxy-3-oxo-1-propyl)-3-phenyl-1H-pyrazole-1-ylmethyl]benzoate (1.68 g, yield: 88%) was obtained as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:4, volume ratio).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6513d8ec40304e34a5b07ca274eac279
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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