(2-Chloro-phenyl)-(2,4,6-trifluoro-pyridin-3-yl)-methanol → (2-Chloro-phenyl)-(2,4,6-trifluoro-pyridin-3-yl)-methanone

HRID 230207

반응식

HRID 230207 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:10]1[C:11]([F:18])=[N:12][C:13]([F:17])=[CH:14][C:15]=1[F:16])[OH:9]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4].O=[Mn]=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[C:11]([F:18])=[N:12][C:13]([F:17])=[CH:14][C:15]=1[F:16])=[O:9]

참가 물질

5

반응물 1

HCID 59812938(2-Chloro-phenyl)-(2,4,6-trifluoro-pyridin-3-yl)-methanol

생성물 1

HCID 59812983(2-Chloro-phenyl)-(2,4,6-trifluoro-pyridin-3-yl)-methanone수율 32%

시약·촉매·용매 3

HCID 14801Manganese dioxide촉매HCID 178418406HCID 178418406, 화합물촉매HCID 1140Toluene용매

실험 절차

(2-Chloro-phenyl)-(2,4,6-trifluoro-pyridin-3-yl)-methanol (8.02 g, 29.3 mmol) was taken up in 80 mL of dry toluene, and manganese dioxide 26 g) was added. The reaction mixture was refluxed for 2.5 hours, after which 2.5 g of additional MnO2 was added. The reaction mixture was refluxed for another hour and an additional 2.5 g of MgO2 was added. The reaction mixture was refluxed for three hours, and was then hot filtered through Celite. The Celite plug was washed with hot EtOAc (in several portions), and the organic solvents were combined. The solvent was evaporated under reduced pressure, and the residue was subject to flash chromatography 5% to 10% EtOAc in hexanes) to give 2.55 g of (2-Chloro-phenyl)-(2,4,6-trifluoro-pyridin-3-yl)-methanone. Mass Spec. M−H=270.

후처리

  1. temperatureThe reaction mixture was refluxed for 2.5 hours
  2. temperatureThe reaction mixture was refluxed for another hour
  3. temperatureThe reaction mixture was refluxed for three hours
  4. filtrationwas then hot filtered through Celite
  5. washThe Celite plug was washed with hot EtOAc (in several portions)
  6. customThe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-1fadbb9345124d018c14d8989a459699
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566708B2

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