Dimethylformamide → ethyl (2E)-3-(1,5-dimethyl-1H-pyrazol-4-yl)acrylate

HRID 30679Notes

Reaction equation

HRID 30679 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([CH:8]=O)[CH:4]=[N:3]1.[H-].[Na+].C(OP([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])(OCC)=O)C.CN(C)C=O>O>[CH3:1][N:2]1[C:6]([CH3:7])=[C:5](/[CH:8]=[CH:20]/[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:4]=[N:3]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 5796431,5-dimethyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 83766845ethyl (2E)-3-(1,5-dimethyl-1H-pyrazol-4-yl)acrylateYield 49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1,5-dimethyl-1H-pyrazole-4-carbaldehyde (400 mg), sodium hydride (60% in oil, 155 mg), ethyl diethylphosphonoacetate (795 mg) and N,N-dimethylformamide (5 ml) was stirred at room temperature for 1 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated. Recrystallization of the residue from ethyl acetate-hexane gave ethyl (2E)-3-(1,5-dimethyl-1H-pyrazol-4-yl)acrylate (304 mg, 49%) as colorless prism crystals. melting point: 82-83° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customRecrystallization of the residue from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b8607748a0124d53845254843ce576ec
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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