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

HRID 641809

반응식

HRID 641809 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 665152,5-Dimethyl-1-phenylpyrrole-3-carboxaldehyde수율 29.2%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

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 mm.

후처리

  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)

출처 및 근거

ORD 기록
ord-b2d3e25b43d64cdbb8373516751c41b2
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696227B2

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