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

HRID 230207ノート

反応式

HRID 230207 の反応式
[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]

参加物

5

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 14801Manganese dioxide触媒HCID 178418406HCID 178418406、化合物触媒HCID 1140Toluene溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-1fadbb9345124d018c14d8989a459699
出典データセット
uspto-grants-2009_07
特許番号
US07566708B2

反応ノート

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