Reaktion #42503

Reaktionsgleichung

Iodobutane

1-Butyl-1H-indole-6-carboxylic acid

Potassium tert-butoxide

→

butyl 1-butyl-1H-indole-6-carboxylate

Lösungsmittel

brine

water

ethyl acetate

dimethyl sulfoxide

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGto stir at room temperature for 6 h
2. 2
   Trocknendried over magnesium sulfate
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated

Vorschrift

1-Butyl-1H-indole-6-carboxylic acid (0.450 g) was dissolved in dimethyl sulfoxide (10 mL). Potassium tert-butoxide (0.317 g) was added and the mixture was stirred for 10 min at room temperature. Iodobutane (0.33 mL) was added and the mixture was allowed to stir at room temperature for 6 h. Water was then added and the mixture was partioned between ethyl acetate, water, and brine, and dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography using heptane/dichloromethane (30/70) gave butyl 1-butyl-1H-indole-6-carboxylate (0.429 g). MS (ESI+) for C17H23NO2+H1 m/z 274.20 (M+H)+.

Quelle