Water → ethyl(E)-3-[1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-yl]propenoate

HRID 350149Notes

Reaction equation

HRID 350149 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH3:17][C:18]1[O:22][C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:20][C:19]=1[CH2:29][O:30][C:31]1[CH:44]=[CH:43][C:34]([CH2:35][N:36]2[CH:40]=[C:39]([CH:41]=O)[CH:38]=[N:37]2)=[CH:33][CH:32]=1.O>O1CCCC1>[CH3:17][C:18]1[O:22][C:21]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[N:20][C:19]=1[CH2:29][O:30][C:31]1[CH:32]=[CH:33][C:34]([CH2:35][N:36]2[CH:40]=[C:39](/[CH:41]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:38]=[N:37]2)=[CH:43][CH:44]=1

Participants

6

Reactant 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 230247841-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazole-4-carbaldehyde

Product 1

HCID 69423038ethyl(E)-3-[1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-yl]propenoateYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60%, oily, 336 mg) was added at 0° C. to a solution of ethyl diethylphosphonoacetate (1.67 ml) in tetrahydrofuran (20 ml), which was stirred at 0° C. for 30 minutes. To this solution, a solution of 1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-carbaldehyde (2.61 g) in tetrahydrofuran (20 ml) was added dropwise at 0° C., and the mixture was stirred at room temperature for 15 minutes. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated sodium chloride solution, dried (MgSO4), and concentrated. The obtained crystals were collected by filtration, and ethyl (E)-3-[1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazole-4-yl]propenoate (2.78 g, yield: 90%) was obtained. This was recrystallized from ethyl acetate-hexane. Melting point: 112–113° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 15 minutes
  2. extractionwas extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. filtrationThe obtained crystals were collected by filtration

Sources & evidence

ORD record
ord-faab7222460c4266b0d5474e3865bf0f
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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