Water → Ethyl 3-butyl-1-methyl-1H-indole-5-carboxylate

HRID 14212

Reaktionsgleichung

Reaktionsgleichung von HRID 14212
[CH2:1]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:12]=2)[NH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[CH3:19]C(C)([O-])C.[K+].IC.O>CS(C)=O>[CH2:1]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:12]=2)[N:7]([CH3:19])[CH:6]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 21086100ethyl 3-butyl-1H-indole-5-carboxylateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 21086101Ethyl 3-butyl-1-methyl-1H-indole-5-carboxylateAusbeute 46,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a mixture of ethyl 3-butyl-1H-indole-5-carboxylate (0.6 g) in methylsulfoxide (10 mL) was added potassium t-butoxide (0.29 g) and iodomethane (2.0 mL). The mixture was stirred at 50° C. for 18 H, at which time the mixture was pored into water (50 mL). The solution was extracted with ethyl acetate and the organic extracts washed three times with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Column chromatography on silica gel (100 mL) using 5% ethyl acetate in hexanes as eluent to give 0.294 g of the title compound: 1H NMR (CDCl3) δ 0.953, 1.44, 1.69, 2.77, 3.76, 4.40, 6.87, 7.26, 7.91, 8.35.

Aufarbeitung

  1. extractionThe solution was extracted with ethyl acetate
  2. washthe organic extracts washed three times with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-114c48f6863b4162903239d87df55f74
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

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