Water → 5-(Benzyloxy)-2,3-dihydro-1H-indole

HRID 1633673

Reaktionsgleichung

Reaktionsgleichung von HRID 1633673
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH3-]C#N.[Na+].O.[OH-].[K+]>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH2:13][CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 146245-BenzyloxyindoleHCID 14797Potassium HydroxideHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 167948815-(Benzyloxy)-2,3-dihydro-1H-indoleAusbeute 89,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

This example was carried out in analogy to: Gordon W. Gribble, Joseph H. Hoffmann Synthesis 1977, 859-860. To a precooled solution of 22.3 g (0.1 mol) 5-benzyloxyindole in 270 ml acetic acid, 19 g (0.3 mol) NaCNBH3 were added. The solution was stirred at RT for 2 h, the volume was reduced to a third and poured into 300 ml water. Potassium hydroxide was added under cooling, and the solution was extracted with ether. The combined organic phases were washed with water, dried over Na2SO4 and evaporated to yield 20.1 g (89%) 5-Benzyloxy-2,3-dihydro-1H-indole as colorless oil, MS: 225 (M).

Aufarbeitung

  1. customHoffmann Synthesis 1977, 859-860
  2. temperatureunder cooling
  3. extractionthe solution was extracted with ether
  4. washThe combined organic phases were washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d87fea5eadef4b14ba1f76e9e3fd3b46
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06503907B2

Verknüpfte Notizen

Wird geladen…