Réaction #42503

Équation de réaction

Iodobutane

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

Potassium tert-butoxide

→

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

Solvants

brine

water

ethyl acetate

dimethyl sulfoxide

Water

Conditions de réaction

Traitement

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

Mode opératoire

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)+.

Source