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

HRID 1453799노트

반응식

HRID 1453799 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

[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.

후처리

  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

출처 및 근거

ORD 기록
ord-bd8591676e444695b60938888a2b7796
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07476684B2

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