Triethyl phosphonoacetate → ethyl(E)-3-(1-benzyl-5-phenyl-1H-pyrazol-4-yl)propenoate

HRID 349921Notes

Reaction equation

HRID 349921 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:13]([CH:21]=O)[CH:12]=[N:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(OP([CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])(OCC)=O)C>CN(C)C=O>[CH2:3]([N:10]1[C:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[C:13](/[CH:21]=[CH:31]/[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:12]=[N:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 230247651-benzyl-5-phenyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 69421709ethyl(E)-3-(1-benzyl-5-phenyl-1H-pyrazol-4-yl)propenoateYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60%, oily, 1.28 g) was added to a mixture of 1-benzyl-5-phenyl-1H-pyrazole-4-carbaldehyde (7.00 g), ethyl diethylphosphonoacetate (6.59 g), and N,N-dimethylformamide (100 ml) at 0° C., and the mixture was stirred at room temperature for 2.5 days. The reaction mixture was poured into ice water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with water and then with saturated aqueous sodium chloride solution, dried (MgSO4), and then concentrated. The residue was subjected to silica gel column chromatography, and ethyl(E)-3-(1-benzyl-5-phenyl-1H-pyrazol-4-yl)propenoate (6.30 g, yield: 71%) was obtained as colorless crystals from the fraction eluted with ethyl acetate-hexane (1:4, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 62–63° C.

Workup

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

Sources & evidence

ORD record
ord-ba61161a4e8d4b528c322224fe9f2260
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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