Ethyl Acetate → 3-Isopropyl-5-(4-nitro-2,6-dimethyl-phenoxy)-1H-indole

HRID 1007484노트

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HRID 1007484 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+].[CH3:20][C:21]1[CH:22]=[C:23]([N+:29]([O-:31])=[O:30])[CH:24]=[C:25]([CH3:28])[C:26]=1F.C(OCC)(=O)C>CS(C)=O.O>[CH:11]([C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([O:1][C:26]3[C:21]([CH3:20])=[CH:22][C:23]([N+:29]([O-:31])=[O:30])=[CH:24][C:25]=3[CH3:28])[CH:3]=2)[NH:7][CH:6]=1)([CH3:13])[CH3:12]

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 113672322-Fluoro-1,3-dimethyl-5-nitrobenzeneHCID 226694913-isopropyl-1H-indol-5-ol

생성물 1

HCID 226695113-Isopropyl-5-(4-nitro-2,6-dimethyl-phenoxy)-1H-indole

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

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온도
100 °C

실험 절차

11.44 g (58.76 mmol) of 5-hydroxy-3-isopropyl-indole are dissolved in 350 ml of DMSO, 8.93 g (64.63 mmol) of potassium carbonate in solid form are introduced and subsequently 9.94 g (58.76 mmol) of 3,5-dimethyl-4-fluoronitrobenzene are added. The reaction solution is stirred for 2 hours at 100° C. under argon. Afterwards it is cooled to room temperature, 100 ml of ethyl acetate and 600 ml of H2O are added; ethyl acetate is separated off after phase separation and the aqueous phase is reextracted twice with ethyl acetate. The combined organic phases are washed twice with sodium chloride solution, dried over sodium sulphate, filtered and concentrated to dryness. The residue is purified by chromatography on silica gel by means of cyclohexane/ethyl acetate (10:1).

후처리

  1. temperatureAfterwards it is cooled to room temperature
  2. customethyl acetate is separated off
  3. customafter phase separation
  4. washThe combined organic phases are washed twice with sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue is purified by chromatography on silica gel by means of cyclohexane/ethyl acetate (10:1)

출처 및 근거

ORD 기록
ord-c65647b50728423e988ab1d275144b03
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06794406B2

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