Water → HCID 69215549, compound

HRID 2221667Notes

Reaction equation

HRID 2221667 reaction equation
[CH2:1]([C:3]1[O:4][CH:5]=[C:6]([CH2:8]P(=O)([O-])[O-])[N:7]=1)[CH3:2].[H-].[Na+].[CH3:15][O:16][CH2:17][O:18][C:19]1[C:23]([CH:24]=O)=[CH:22][N:21]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:20]=1.O>O1CCCC1>[CH2:1]([C:3]1[O:4][CH:5]=[C:6](/[CH:8]=[CH:24]\[C:23]2[C:19]([O:18][CH2:17][O:16][CH3:15])=[N:20][N:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:22]=2)[N:7]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 230765133-(methoxymethoxy)-1-phenyl-1H-pyrazole-4-carbaldehydeHCID 86605748HCID 86605748, compound

Product 1

HCID 69215549HCID 69215549, compoundYield 7.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of diethyl ([(2-ethyl-1,3-oxazol-4-yl)methyl]phosphonate (2.97 g) in tetrahydrofuran (50 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 (1:9-3:7, v/v) to give 2-ethyl-4-{(Z)-2-[3-(methoxymethoxy)-1-phenyl-1H-pyrazol-4-yl]ethenyl}-1,3-oxazole as a pale-yellow oil (0.24 g, yield 7.4%).

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 (1:9-3:7

Sources & evidence

ORD record
ord-e6b1c89b5fc440c0b659661a965cf72b
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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