Dimethylformamide → ethyl 3-[1-(4-benzyloxy-3-methoxybenzyl)-3-ethoxy-1H-pyrazol-4-yl]propionate

HRID 350175Notes

Reaction equation

HRID 350175 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].[CH2:16]([O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][C:25]=1[O:32][CH3:33])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CN(C)C=O.[H-].[Na+]>O>[CH2:16]([O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][N:6]2[CH:7]=[C:8]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:4]([O:3][CH2:1][CH3:2])=[N:5]2)=[CH:26][C:25]=1[O:32][CH3:33])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 2979621-(Benzyloxy)-4-(chloromethyl)-2-methoxybenzeneHCID 178471163HCID 178471163, compound

Product 1

HCID 23025006ethyl 3-[1-(4-benzyloxy-3-methoxybenzyl)-3-ethoxy-1H-pyrazol-4-yl]propionateYield 89.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethyl 3-(3-ethoxy-1H-pyrazol-4-yl)propionate (1.59 g), 4-benzyloxy-3-methoxybenzyl chloride (1.97 g), and N,N-dimethylformamide (30 ml), sodium hydride (60%, oily, 0.30 g) 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, and dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and ethyl 3-[1-(4-benzyloxy-3-methoxybenzyl)-3-ethoxy-1H-pyrazol-4-yl]propionate (2.93 g, yield: 89%) was obtained as a colorless oily substance from the fractions eluted with ethyl acetate-hexane (1:2, 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, and dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-535cb7ec5aed4975964d95257b3716cc
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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