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

HRID 1453799ノート

反応式

HRID 1453799 の反応式
[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

参加物

4

反応物 2

HCID 57528605[5-(3-Chlorophenyl)isoxazol-3-yl]methanolHCID 178418287HCID 178418287、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

[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.

後処理

  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

出典と根拠

ORDレコード
ord-bd8591676e444695b60938888a2b7796
出典データセット
uspto-grants-2009_01
特許番号
US07476684B2

反応ノート

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