Potassium Carbonate → 1-(4-fluorophenyl)-1H-pyrrole-2-carbaldehyde

HRID 1744483ノート

反応式

HRID 1744483 の反応式
P(Cl)(Cl)(Cl)=O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH:17]=[CH:16][CH:15]=[CH:14]2)=[CH:9][CH:8]=1.[C:18](=O)([O-])[O-:19].[K+].[K+]>CN(C)C=O>[F:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[CH:17]=[CH:16][CH:15]=[C:14]2[CH:18]=[O:19])=[CH:11][CH:12]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 727844N-(4-fluorophenyl)pyrrole

生成物 1

HCID 31618451-(4-fluorophenyl)-1H-pyrrole-2-carbaldehyde収率 36.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Phosphorus oxychloride (96.5 g) was added dropwise under ice-cooling to dimethylformamide (600 ml) containing 1-(4-fluorophenyl)pyrrole (101 g) over 1 h, and the mixture was stirred for 2 h and at room temperature for one day. The reaction mixture was added to 3 Liters of aqueous solution containing potassium carbonate (130 g) and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue to allow crystallization. The crystals were recrystallized from a mixed solvent of toluene-diisopropyl ether (ratio=1:10) to give 1-(4-fluorophenyl)-2-formylpyrrole (43 g), melting point: 82–83° C.

後処理

  1. additionThe reaction mixture was added to 3 Liters of aqueous solution
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. additionDiisopropyl ether was added to the residue
  7. customcrystallization
  8. customThe crystals were recrystallized from a mixed solvent of toluene-diisopropyl ether (ratio=1:10)

出典と根拠

ORDレコード
ord-54b9beed2ae3471aa8691c5ca9cb7251
出典データセット
uspto-grants-2006_03
特許番号
US07015218B1

反応ノート

読み込み中…