Dimethylformamide → 2,5-Dimethyl-1-phenylpyrrole-3-carboxaldehyde

HRID 1642350

反応式

HRID 1642350 の反応式
[CH3:1][C:2]1[N:3]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.CN([CH:17]=[O:18])C.P(Cl)(Cl)(Cl)=O.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:3]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]([CH3:7])=[CH:5][C:6]=1[CH:17]=[O:18]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 665182,5-Dimethyl-1-phenylpyrrole

生成物 1

HCID 665152,5-Dimethyl-1-phenylpyrrole-3-carboxaldehyde収率 29.2%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

To a well stirred solution of 2,5-dimethyl-1-phenyl-1H-pyrrole (7.65 g, 44.7 mmol) and DMF (3.6 g, 49.2 mmol) in 70 mL of dry toluene, phosphorus oxychloride (6.9 g, 44.7 mmol) was added in small portions. The mixture was heated to 80° C. for 3 hrs. The solution was allowed to cool to room temperature, then 100 mL of saturated aqueous Na2CO3 was added. The aqueous layer was extracted with EtOAc (100 mL×3). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure, the residue was purified by column chromatography (hexane:EtOAc=10:1) to give 2.6 g of 2,5-dimethyl-1-phenyl-1H-pyrrole-3-carbaldehyde (29%). MS [M++1]=200, LC-MS: tR=1.96 min.

後処理

  1. temperatureto cool to room temperature
  2. extractionThe aqueous layer was extracted with EtOAc (100 mL×3)
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. customthe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography (hexane:EtOAc=10:1)

出典と根拠

ORDレコード
ord-271540423c924802a38d37ad61840419
出典データセット
uspto-grants-2012_02
特許番号
US08119660B2

関連ノート

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