Water → ethyl 1-benzyl-3-ethoxy-1H-pyrazol-4-ylacetate

HRID 350018Notes

Reaction equation

HRID 350018 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[CH:14]=[C:13]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:12]([OH:21])=[N:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:22](I)[CH3:23].O>CN(C)C=O>[CH2:3]([N:10]1[CH:14]=[C:13]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:12]([O:21][CH2:22][CH3:23])=[N:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 178470731HCID 178470731, compound

Product 1

HCID 69422643ethyl 1-benzyl-3-ethoxy-1H-pyrazol-4-ylacetateYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60%, oily, 1.20 g) was added to a solution of ethyl 1-benzyl-3-hydroxy-1H-pyrazol-4-ylacetate (7.81 g) in N,N-dimethylformamide (100 ml) at 0° C., which was stirred at room temperature for 15 minutes. Ethyl iodide (2.40 ml) was added to the mixture, which was stirred at room temperature for 1 hour. 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 concentrated. The residue was subjected to silica gel column chromatography to obtain ethyl 1-benzyl-3-ethoxy-1H-pyrazol-4-ylacetate (7.52 g, yield 87%) as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:3, volume ratio).

Workup

  1. stirringwas stirred at room temperature for 1 hour
  2. extractionwas extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fcfe5c4305a746d6ae71b41f9329d634
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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