Iodoethane → 7-ethoxy-1H-indole

HRID 550150

Reaktionsgleichung

Reaktionsgleichung von HRID 550150
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[OH:10])[CH:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].I[CH2:18][CH3:19]>CC(C)=O>[CH2:18]([O:10][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[NH:1][CH:2]=[CH:3]2)[CH3:19]

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 27376517-Hydroxyindole

Produkt 1

HCID 198489347-ethoxy-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a stirred solution of 1H-indol-7-ol (500 mg, 3.75 mmol) in acetone (10 mL) at r.t. was added potassium carbonate (3.11 g, 22.5 mmol), followed by iodoethane (0.45 mL, 5.63 mol), The mixture was stirred at r.t. for 16 h then solvent removed under reduced pressure. The crude product thus obtained was purified by chromatography over silica gel to afford 7-ethoxy-1H-indole: 1H NMR (400 MHz, MeOD) δ ppm 1.51 (t, J=6.95 Hz, 3 H), 4.22 (q, J=6.91 Hz, 2 H), 6.42 (d, J=3.03 Hz, 1H), 6.63 (d, J=7.58 Hz, 1 H), 6.92 (t, J=7.83 Hz, 1 H), 7.04-7.23 (m, 2 H); MS (ES+): m/z 162.20 (MH+).

Aufarbeitung

  1. customsolvent removed under reduced pressure
  2. customThe crude product thus obtained
  3. customwas purified by chromatography over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-78f1ce15b56548bc9228123ab66c5466
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943767B2

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