Dimethylformamide → ethyl(E)-3-(1-benzyl-3-benzyloxy-1H-pyrazol-4-yl)propenoate

HRID 349939Notes

Reaction equation

HRID 349939 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[CH:14]=[C:13]([CH:15]=O)[C:12]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(OP([CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])(OCC)=O)C.CN(C)C=O>O>[CH2:3]([N:10]1[CH:14]=[C:13](/[CH:15]=[CH:33]/[C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:12]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 229307681-benzyl-3-(benzyloxy)-1H-pyrazole-4-carbaldehyde

Product 1

HCID 69421683ethyl(E)-3-(1-benzyl-3-benzyloxy-1H-pyrazol-4-yl)propenoateYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60%, oily, 1.94 g) was added to a mixture of 1-benzyl-3-benzyloxy-1H-pyrazole-4-carbaldehyde (12.90 g), ethyl diethylphosphonoacetate (9.60 ml), and N,N-dimethylformamide (200 ml) at 0° C., and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with diluted hydrochloric acid and then with saturated aqueous sodium chloride solution, dried (MgSO4), and then concentrated. The crystals obtained were collected by filtration to yield ethyl(E)-3-(1-benzyl-3-benzyloxy-1H-pyrazol-4-yl)propenoate (14.50 g, yield: 91%). This was recrystallized from ethyl acetate-hexane. Melting point: 88–89° C.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with diluted hydrochloric acid
  3. dry with materialwith saturated aqueous sodium chloride solution, dried (MgSO4)
  4. concentrationconcentrated
  5. customThe crystals obtained
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-08fa90de964c4beea62bd405a42ee8bd
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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