Reaction #42499

Reaction equation

Methyl 1H-indole-6-carboxylate

potassium tert-butoxide

Iodobutane

→

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

Solvents

DMSO

Conditions

Workup

1. 1
   workup.STIRRINGto stir for three additional hours
2. 2
   OtherThe mixture was partitioned between ethyl acetate and water and brine
3. 3
   Dryingdried over sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated

Procedure

Methyl 1H-indole-6-carboxylate (4.17 g) was dissolved in DMSO (30 mL), and potassium tert-butoxide (2.93 g) was added. The mixture was stirred for ten min at room temperature. Iodobutane (3.0 mL) was added. The mixture was allowed to stir for three additional hours. The mixture was partitioned between ethyl acetate and water and brine, dried over sodium sulfate, filtered, and concentrated to give methyl 1-butyl-1H-indole-6-carboxylate (4.53 g). MS (ESI+) for C14H17NO2+H1 m/z 232.12 (M+H)+.

Source