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

HRID 2221682Notes

Reaction equation

HRID 2221682 reaction equation
C(OP([CH2:9][C:10]1[N:11]=[C:12]([C:15]2[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=2[C:17]([O:19][CH3:20])=[O:18])[S:13][CH:14]=1)(OCC)=O)C.[H-].[Na+].[CH3:27][O:28][CH2:29][O:30][C:31]1[C:35]([CH:36]=O)=[CH:34][N:33]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[N:32]=1.O>O1CCCC1>[CH3:27][O:28][CH2:29][O:30][C:31]1[C:35](/[CH:36]=[CH:9]/[C:10]2[N:11]=[C:12]([C:15]3[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=3[C:17]([O:19][CH3:20])=[O:18])[S:13][CH:14]=2)=[CH:34][N:33]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[N:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 230765133-(methoxymethoxy)-1-phenyl-1H-pyrazole-4-carbaldehydeHCID 86605752Methyl {4-[(diethoxyphosphoryl)methyl]-1,3-thiazol-2-yl}benzoate

Product 1

HCID 86605751methyl (4-{(E)-2-[3-(methoxymethoxy)-1-phenyl-1H-pyrazol-4-yl]ethenyl}-1,3-thiazol-2-yl)benzoateYield 20.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl {4-[(diethoxyphosphoryl)methyl]-1,3-thiazol-2-yl}benzoate (4.7 g) in tetrahydrofuran (100 mL) was added sodium hydride (60% in oil, 1.1 g) at room temperature, and the mixture was stirred for 30 min. 3-(Methoxymethoxy)-1-phenyl-1H-pyrazole-4-carbaldehyde (2.8 g) was added to the reaction mixture, and the mixture was heated under reflux for 3 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 (30:70-60:40, v/v) to give methyl (4-{(E)-2-[3-(methoxymethoxy)-1-phenyl-1H-pyrazol-4-yl]ethenyl}-1,3-thiazol-2-yl)benzoate as pale-yellow crystals (1.1 g, yield 20%). Recrystallization from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 134-135° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 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 (30:70-60:40

Sources & evidence

ORD record
ord-23ae15c32d764107a0f9095041c12819
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

Loading…