Sodium Chloride → ethyl 3-[1-[6-(2-fluorobenzyloxy)-2-naphthylmethyl]-3-phenyl-1H-pyrazole-4-yl]propionate

HRID 350133Notes

Reaction equation

HRID 350133 reaction equation
Cl[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[F:21])[CH:9]=2)[CH:4]=1.[C:22]1([C:28]2[C:32]([CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:31][NH:30][N:29]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[H-].[Na+].[Cl-].[Na+]>CN(C)C=O>[F:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][O:13][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[CH:4]=[C:3]([CH2:2][N:30]1[CH:31]=[C:32]([CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:28]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[N:29]1)[CH:12]=[CH:11]2

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 230249302-Chloromethyl-6-(2-fluorobenzyloxy)naphthaleneHCID 178471160HCID 178471160, compound

Product 1

HCID 69423106ethyl 3-[1-[6-(2-fluorobenzyloxy)-2-naphthylmethyl]-3-phenyl-1H-pyrazole-4-yl]propionateYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloromethyl-6-(2-fluorobenzyloxy)naphthalene (540 mg) and ethyl 3-(3-phenyl-1H-pyrazol-4-yl]propionate (390 mg) were dissolved in N,N-dimethylformamide (10 ml). Sodium hydride (60%, oily, 70 mg) was added to the solution at 0° C., which was stirred at room temperature for two hours. The reaction mixture was poured into saturated aqueous sodium chloride solution, 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-[1-[6-(2-fluorobenzyloxy)-2-naphthylmethyl]-3-phenyl-1H-pyrazole-4-yl]propionate (0.58 g, yield: 72%) was obtained as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:4, volume ratio).

Workup

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

Sources & evidence

ORD record
ord-8b6f5ad03bbe4de0a52571dad020f3e8
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

Loading…