Dimethylformamide → 3-benzyloxy-1-phenyl-1H-pyrazol-4-ylmethyl acetate

HRID 1295252Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1295252
[CH2:1]([O:8][C:9]1[C:13]([CH2:14]C(O)=O)=[CH:12][N:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI.[C:26](=[O:29])([O-])[O-:27].[K+].[K+].[CH3:32]N(C)C=O>O>[C:26]([O:27][CH2:14][C:13]1[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:10][N:11]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:12]=1)(=[O:29])[CH3:32]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 694305053-benzyloxy-1-phenyl-1H-pyrazol-4-ylacetic acid

Produkt 1

HCID 694263823-benzyloxy-1-phenyl-1H-pyrazol-4-ylmethyl acetateAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 3-benzyloxy-1-phenyl-1H-pyrazol-4-ylacetic acid (2.47 g), methyl iodide (0.75 ml), potassium carbonate (2.21 g) and N,N-dimethylformamide (25 ml) was stirred at room temperature for 1 hr. The reaction solution was poured into water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and 3-benzyloxy-1-phenyl-1H-pyrazol-4-ylmethyl acetate (2.55 g, yield 99%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point: 74–75° C.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c19111e8d65547078fc6e7f5b0ad53b8
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07241785B2

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