Dimethylformamide → ethyl (E)-3-(3-benzyloxy-1-phenyl-1H-pyrazol-5-yl)propenoate

HRID 1295277Notes

Reaction equation

HRID 1295277 reaction equation
[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([CH:14]=O)[N:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([O:25][CH2:26][CH2:27]P(OCC)(OCC)=O)(=[O:24])[CH3:23].CN(C)C=O.[H-].[Na+]>O>[CH2:1]([O:8][C:9]1[CH:13]=[C:12](/[CH:14]=[CH:23]/[C:22]([O:25][CH2:26][CH3:27])=[O:24])[N:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 124696282-(Diethoxyphosphoryl)ethyl acetateHCID 22930766HCID 22930766, compound

Product 1

HCID 86591672ethyl (E)-3-(3-benzyloxy-1-phenyl-1H-pyrazol-5-yl)propenoateYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3-benzyloxy-1-phenyl-1H-pyrazole-5-carbaldehyde (6.24 g), diethylphosphonoethyl acetate (5.55 g) and N,N-dimethylformamide (50 ml) was added sodium hydride (60% in oil, 960 mg) at 0° C. and the mixture was stirred overnight at room temperature. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with dilute hydrochloric acid and then saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and ethyl (E)-3-(3-benzyloxy-1-phenyl-1H-pyrazol-5-yl)propenoate (7.33 g, yield 94%) was obtained as a pale-yellow oil from a fraction eluted with ethyl acetate-hexane (1:4, volume ratio).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed successively with dilute hydrochloric acid
  3. dry with materialsaturated brine, dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cb1cbae60cc7460dab25e56964225bee
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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