Hydrogen Peroxide → 7-Ethenyl-1H-indole

HRID 351589노트

반응식

HRID 351589 반응식
C[C:2]1([CH3:12])[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[OH-].[Na+].OO>O1CCCC1.C(OCC)(=O)C>[CH:10]([C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[NH:3][CH:2]=[CH:12]2)=[CH2:11]

참가 물질

6

반응물 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 124373012,2-Dimethyl-1,2-dihydroquinoline

생성물 1

HCID 145674047-Ethenyl-1H-indole수율 63.5%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a 0° C. solution of 7-vinylindole 1 (0.95 g, 6.6 mmol) in anhydrous tetrahydrofuran (60 mL) was added 1 M borane-tetrahydrofuran complex in tetrahydrofuran (9.95 mL, 9.95 mmol) and the reaction stirred overnight at room temperature. 1 N sodium hydroxide (25 mL) and 30% hydrogen peroxide (35 mL) were then added and the mixture stirred at reflux for 1 hour. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (100 mL), washed with water (50 mL) and saturated aqueous sodium chloride (2×50 mL), dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 50% ethyl acetate in hexanes. Fractions containing product were combined and concentrated under reduced pressure to provide 0.60 g (56%) of the desired compound as a yellow oil.

후처리

  1. stirringthe mixture stirred
  2. temperatureat reflux for 1 hour
  3. temperatureThe reaction mixture was cooled to room temperature
  4. washwashed with water (50 mL) and saturated aqueous sodium chloride (2×50 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washeluting with 50% ethyl acetate in hexanes
  8. additionFractions containing product
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-ef9f3bf8626e41feb3e8b87b3be51dcb
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743785B2

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