Boron trifluoride etherate → 2,3-dihydro-1H-indol-5-ol

HRID 454191노트

반응식

HRID 454191 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C([BH3-])#N.[Na+].B(F)(F)F.CCOCC>CO>[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2

참가 물질

5

반응물 3

HCID 8000Boron trifluoride etherateHCID 160545-HydroxyindoleHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 100346842,3-dihydro-1H-indol-5-ol수율 73%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

5-Hydroxyindole (2 g, 15 mmol) was dissolved in methanol (60 ml) under argon. Sodium cyanoborohydride (1.89 g, 30 mmol) and trifluoroboron etherate (4.2 ml, 33 mmol) were added and the mixture was heated at reflux for 3 hours then left to cool to ambient temperature. The solvent was evaporated and the residue was partitioned between ethyl acetate and water. Ammonia was added to adjust the pH to 10 and the aqueous phase was extracted with more ethyl acetate. The combined organic phases were washed with water, brine, dried (MgSO4), filtered and the solvent evaporated. The residue was purified by flash chromatography using dichloromethane/methanol (95/5) as solvent. Evaporation of the solvent gave 5-hydroxy-2,3-dihydro-1H-indole (1.45 g, 73%) as an off white solid.

후처리

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 hours
  3. waitthen left
  4. customThe solvent was evaporated
  5. customthe residue was partitioned between ethyl acetate and water
  6. additionAmmonia was added
  7. extractionthe aqueous phase was extracted with more ethyl acetate
  8. washThe combined organic phases were washed with water, brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customthe solvent evaporated
  12. customThe residue was purified by flash chromatography
  13. customEvaporation of the solvent

출처 및 근거

ORD 기록
ord-b372ae32ecc046f1857ba9e2446e568d
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492560B2

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