Benzyl Bromide → ethyl 1-benzyl-1H-pyrazole-4-carboxylate

HRID 274750Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 274750
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[CH:9]=[N:10][NH:11][CH:12]=1)=[O:7])[CH3:4].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C=O>[CH2:13]([N:10]1[CH:9]=[C:8]([C:6]([O:5][CH2:3][CH3:4])=[O:7])[CH:12]=[N:11]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 142179ethyl 1H-pyrazole-4-carboxylate

Produkt 1

HCID 15237993ethyl 1-benzyl-1H-pyrazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a suspension of sodium hydride (containing 63%, 652 mg) in dimethylformamide (abbreviated as DMF hereinafter) was added a solution of 4-ethoxycarbonylpyrazole (2.00 g) in DMF (15 ml) at room temperature. After stirred for 30 min at room temperature, to the mixture was added benzylbromide (2.04 ml). After stirred for 30 min, the mixture was quenched by addition of water. The mixture was extracted with ethyl acetate-n-hexane. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and evaporated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to give the title compound (2.98 g) having the following physical data.

Aufarbeitung

  1. stirringAfter stirred for 30 min
  2. customthe mixture was quenched by addition of water
  3. extractionThe mixture was extracted with ethyl acetate-n-hexane
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-da84e581f053455c945e01a9620ca8ee
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05389666

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