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

HRID 454191Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 454191
[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

Komponenten

5

Edukt 3

HCID 8000Boron trifluoride etherateHCID 160545-HydroxyindoleHCID 5003444Sodium cyanoborohydride

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b372ae32ecc046f1857ba9e2446e568d
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492560B2

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