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

HRID 2221699Notes

Reaction equation

HRID 2221699 reaction equation
[CH2:1]([C:3]1[S:4][C:5](C)=[C:6]([CH2:8]P(=O)(OCC)OCC)[N:7]=1)[CH3:2].[H-].[Na+].[CH3:20][O:21][CH2:22][O:23][C:24]1[C:28]([CH:29]=O)=[CH:27][N:26]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[CH3:37])[N:25]=1.O>O1CCCC1>[CH2:1]([C:3]1[S:4][CH:5]=[C:6](/[CH:8]=[CH:29]/[C:28]2[C:24]([O:23][CH2:22][O:21][CH3:20])=[N:25][N:26]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[CH3:37])[CH:27]=2)[N:7]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 230763813-(methoxymethoxy)-1-(2-methylphenyl)-1H-pyrazole-4-carbaldehydeHCID 86605755Diethyl [(2-ethyl-5-methyl-1,3-thiazol-4-yl)methyl]phosphonate

Product 1

HCID 230764352-ethyl-4-{(E)-2-[3-(methoxymethoxy)-1-(2-methylphenyl)-1H-pyrazol-4-yl]ethenyl}-1,3-thiazoleYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of diethyl [(2-ethyl-5-methyl-1,3-thiazol-4-yl)methyl]phosphonate (1.26 g) in tetrahydrofuran (40 mL) was added sodium hydride (60% in oil, 0.192 g) at room temperature, and the mixture was stirred for 30 min. 3-(Methoxymethoxy)-1-(2-methylphenyl)-1H-pyrazole-4-carbaldehyde (0.99 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 (1:20-1:3, v/v) to give 2-ethyl-4-{(E)-2-[3-(methoxymethoxy)-1-(2-methylphenyl)-1H-pyrazol-4-yl]ethenyl}-1,3-thiazole as a pale-yellow oil (0.81 g, yield 57%).

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 (1:20-1:3

Sources & evidence

ORD record
ord-0efe1d842f3b47339e889677ca928c81
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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