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

HRID 350133Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 350133
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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8b6f5ad03bbe4de0a52571dad020f3e8
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179823B1

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