Sodium Carbonate → 1-(4-Fluorophenyl)-5-formyl-2-(4-methylsulfonylphenyl)pyrrole

HRID 856832ノート

反応式

HRID 856832 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][CH:10]=[C:9]2[C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.[C:28](=O)([O-])[O-:29].[Na+].[Na+]>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH:28]=[O:29])=[CH:11][CH:10]=[C:9]2[C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 108291321-(4-Fluorophenyl)-2-(4-methylsulfonylphenyl)pyrrole

生成物 1

HCID 218628661-(4-Fluorophenyl)-5-formyl-2-(4-methylsulfonylphenyl)pyrrole収率 50%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

1.67 g (5.3 mmol) of 1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)pyrrole (prepared as described in Example 33) were dissolved in 30 ml of dimethylformamide, 0.50 ml (5.3 mmol) of phosphorous oxychloride was added to the resulting solution, and the mixture was then stirred at 60° C. for 2 hours. At the end of this time, the reaction mixture was gradually added to ice-water and the pH of the mixture was adjusted to a value of 8-9 by the addition of sodium carbonate. The mixture was then extracted with ethyl acetate. The organic extract was washed with water and dried over anhydrous sodium sulfate, after which the solvent was removed by distillation under reduced pressure. The residue was applied to a silica gel chromatography column and eluted with a 5:1 by volume mixture of hexane and ethyl acetate, to give 0.90 g (yield 50%) of the title compound as a white powder, melting at 135-137° C.

後処理

  1. extractionThe mixture was then extracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customafter which the solvent was removed by distillation under reduced pressure
  6. washeluted with a 5:1 by volume mixture of hexane and ethyl acetate

出典と根拠

ORDレコード
ord-797c736b216b4f1a92a3c14702ef3a1d
出典データセット
uspto-grants-2006_12
特許番号
USRE039420E1

反応ノート

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