Butyl iodide → 1h-Indole,7-butoxy-

HRID 1725835

Reaktionsgleichung

Reaktionsgleichung von HRID 1725835
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.C(=O)([O-])[O-].[K+].[K+].I[CH2:18][CH2:19][CH2:20][CH3:21]>C(C(C)=O)C>[CH2:18]([O:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2)[CH2:19][CH2:20][CH3:21]

Komponenten

5

Edukt 3

HCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 27376517-Hydroxyindole

Produkt 1

HCID 219401081h-Indole,7-butoxy-Ausbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To a stirred solution of 7-hydroxyindole and potassium carbonate (325 mg, 2.35 mmol) in methyl ethyl ketone (2.4 mL) was added iodobutane (1.24 mL, 10.8 mmol) at room temperature. After the mixture was heated at 55° C. for 12 h the solvent was removed and water was added. The mixture was extracted with EtOAc (3 times), dried over anhydrous MgSO4, filtered and evaporated. After chromatographic purification on silica gel, 7-n-butoxyindole was obtained in 90% yield (310 mg). 1H NMR (500 MHz, CDCl3) δ 8.39 (1H, brs), 7.23 (1H, d, J=8.0 Hz, 7.17 (1H, t, J=3.0 Hz), 7.01 (1H, t, J=7.5 Hz), 6.63 (1H, d, J=7.0 Hz), 6.53 (1H, t, J=2.5 Hz), 4.14 (2H, t, J=5.2 Hz), 1.88-1.80 (2H, m), 1.59-1.50 (2H, m), 1.00 (3H, t, J=7.0 Hz).

Aufarbeitung

  1. customwas removed
  2. additionwater was added
  3. extractionThe mixture was extracted with EtOAc (3 times)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customAfter chromatographic purification on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-e07a16aa02174836b46959dcaec112d6
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07491743B2

Verknüpfte Notizen

Wird geladen…