Dimethylformamide → ethyl 3-[3-ethoxy-1-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-yl]propionate

HRID 350202Notes

Reaction equation

HRID 350202 reaction equation
[CH2:1]([O:3][C:4]1[C:8]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][NH:6][N:5]=1)[CH3:2].Cl[CH2:17][C:18]1[CH:19]=[C:20]([CH:35]=[CH:36][CH:37]=1)[O:21][CH2:22][C:23]1[N:24]=[C:25]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:26][C:27]=1[CH3:28].CN(C)C=O.[H-].[Na+]>O>[CH2:1]([O:3][C:4]1[C:8]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][N:6]([CH2:17][C:18]2[CH:37]=[CH:36][CH:35]=[C:20]([O:21][CH2:22][C:23]3[N:24]=[C:25]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[O:26][C:27]=3[CH3:28])[CH:19]=2)[N:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 108815514-(3-Chloromethylphenoxymethyl)-5-methyl-2-phenyloxazoleHCID 178471163HCID 178471163, compound

Product 1

HCID 23021925ethyl 3-[3-ethoxy-1-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-yl]propionateYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethyl 3-(3-ethoxy-1H-pyrazol-4-yl]propionate (509 mg), 4-(3-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (753 mg), and N,N-dimethylformamide (10 ml), sodium hydride (60%, oily, 96.0 mg) was added at 0° C., and then the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with water, then, with saturated aqueous sodium chloride solution, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and ethyl 3-[3-ethoxy-1-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-yl]propionate (809 mg, yield: 69%) was obtained as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:3, volume ratio).

Workup

  1. additionwas added at 0° C.
  2. extractionwas extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialwith saturated aqueous sodium chloride solution, dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e7cf6afefada40a3924a41fe0bf2f36c
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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