4-Methoxy-1H-indole → 4-methoxy-2,3-dihydro-1H-indole

HRID 250198

Reaktionsgleichung

Reaktionsgleichung von HRID 250198
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2.C([BH3-])#N.[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][NH:7]2

Komponenten

4

Edukt 2

HCID 1383634-Methoxy-1H-indoleHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 162444414-methoxy-2,3-dihydro-1H-indoleAusbeute 54,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

4-methoxyindole (0.735 g) was dissolved in acetic acid (25 ml) and cooled in an ice bath. To this solution was added sodium cyanoborohydride (0.942 g) in portions. After the addition was complete, the solution was allowed to come to room temperature and the solution was stirred for an hour. The solvent was removed under vacuum and the residue was taken up in ethyl acetate, washed with sodium carbonate solution, water and finally with brine. The organic layer was evaporated and the resulting product was purified on a silica gel column eluting with ethyl acetate:dichloromethane (5:95) to give 0.404 g of 4-methoxyindoline.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. additionAfter the addition
  3. customto come to room temperature
  4. customThe solvent was removed under vacuum
  5. washwashed with sodium carbonate solution, water and finally with brine
  6. customThe organic layer was evaporated
  7. customthe resulting product was purified on a silica gel column
  8. washeluting with ethyl acetate:dichloromethane (5:95)

Quellen und Nachweise

ORD-Eintrag
ord-65321f0565a2421a96157812585bb734
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863305B2

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