Triethyl phosphonoacetate → HCID 69421629, compound

HRID 349917Notes

Reaction equation

HRID 349917 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[C:14]([CH2:15][CH2:16][CH3:17])=[C:13]([CH:18]=O)[CH:12]=[N:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(OP([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])(OCC)=O)C>CN(C)C=O>[CH2:3]([N:10]1[C:14]([CH2:15][CH2:16][CH3:17])=[C:13](/[CH:18]=[CH:28]/[C:29]([O:31][CH2:32][CH3:33])=[O:30])[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 23024822HCID 23024822, compound

Product 1

HCID 69421629HCID 69421629, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60%, oily, 2.25 g) was added to a mixture of 1-benzyl-5-propyl-1H-pyrazole-4-carbaldehyde (12.60 g), ethyl diethylphosphonoacetate (10.69 g), and N,N-dimethylformamide (150 ml) at 0° C., and the mixture was stirred at room temperature for 15 hours. 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-propyl-1H-pyrazol-4-yl)propenoate (11.90 g, yield: 85%) 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 water
  3. dry with materialwith saturated aqueous sodium chloride solution, dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-833284bbea324018b06087ef14fd2011
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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