Water → 2-methyl-4-{(E)-2-[3-(methoxymethoxy)-1-phenyl-1H-pyrazol-4-yl]ethenyl}-1,3-thiazole

HRID 2221679Notes

Reaction equation

HRID 2221679 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7]P(=O)(OCC)OCC)[N:6]=1.[H-].[Na+].[CH3:18][O:19][CH2:20][O:21][C:22]1[C:26]([CH:27]=O)=[CH:25][N:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:23]=1.O>O1CCCC1>[CH3:1][C:2]1[S:3][CH:4]=[C:5](/[CH:7]=[CH:27]/[C:26]2[C:22]([O:21][CH2:20][O:19][CH3:18])=[N:23][N:24]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:25]=2)[N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27631974-(Diethoxyphosphorylmethyl)-2-methyl-1,3-thiazoleHCID 230765133-(methoxymethoxy)-1-phenyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 230766172-methyl-4-{(E)-2-[3-(methoxymethoxy)-1-phenyl-1H-pyrazol-4-yl]ethenyl}-1,3-thiazoleYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of diethyl [(2-methyl-1,3-thiazol-4-yl)methyl]phosphonate (2.32 g) in tetrahydrofuran (100 mL) was added sodium hydride (60% in oil, 0.48 g) at room temperature, and the mixture was stirred for 30 min. 3-(Methoxymethoxy)-1-phenyl-1H-pyrazole-4-carbaldehyde (2.32 g) was added to the reaction mixture, and the mixture was heated under reflux for 1.5 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (4:1, v/v) to give 2-methyl-4-{(E)-2-[3-(methoxymethoxy)-1-phenyl-1H-pyrazol-4-yl]ethenyl}-1,3-thiazole as a pale-yellow oil (2.72 g, yield 83%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hrs
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. washeluted with ethyl acetate-hexane (4:1

Sources & evidence

ORD record
ord-94d3f72b499c446394ed2a71a01da84a
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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