[5-(3-Chlorophenyl)isoxazol-3-yl]methanol → 5-(3-Chlorophenyl)isoxazole-3-carbaldehyde

HRID 1453799Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1453799
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([CH2:13][OH:14])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([CH:13]=[O:14])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 57528605[5-(3-Chlorophenyl)isoxazol-3-yl]methanolHCID 178418287HCID 178418287, Verbindung

Produkt 1

HCID 532992685-(3-Chlorophenyl)isoxazole-3-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

[5-(3-chlorophenyl)isoxazol-3-yl]methanol (178.6 g, 852 mmol) in dichloromethane (2 L) was dropwise added to pyridinium chlorochromate (400 g, 1.86 mol) in dichloromethane (2 L). The resulting slurry was stirred over night at room temperature. The slurry was filtrated through celite and the filtrate was distilled off. To the remaining solution EtOAc was added. The organic layer was washed with water, saturated brine and concentrated, to give crude title compound, which was used directly in the next step. 1H NMR (DMSO-d6): 10.13 (s, 1H), 8.08 (br s, 1H), 7.95 (m, 1H), 7.61 (m, 3H). MS (M++1)=208.

Aufarbeitung

  1. filtrationThe slurry was filtrated through celite
  2. distillationthe filtrate was distilled off
  3. additionTo the remaining solution EtOAc was added
  4. washThe organic layer was washed with water, saturated brine
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-bd8591676e444695b60938888a2b7796
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07476684B2

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