Réaction #42500

Équation de réaction

acetyl chloride

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

Diethyl aluminum chloride

→

methyl 3-acetyl-1-butyl-1H-indole-6-carboxylate

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe mixture was stirred for 2 h at 0° C
2. 2
   AutreThe mixture was then partitioned between dichloromethane, water, and brine
3. 3
   Séchagedried over sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated
6. 6
   AutreThe concentrate was chromatographed on silica gel

Mode opératoire

Methyl 1-butyl-1H-indole-6-carboxylate (4.53 g) was dissolved in dichloromethane (25 ml). The mixture was cooled to 0° C. Diethyl aluminum chloride was added dropwise (29.5 mL) and the mixture was allowed to stir at 0° C. for 30 min. A solution of dichloromethane (25 mL) and acetyl chloride (2.1 mL) was added dropwise, and the mixture was stirred for 2 h at 0° C. The mixture was then partitioned between dichloromethane, water, and brine, dried over sodium sulfate, filtered, and concentrated. The concentrate was chromatographed on silica gel using ethyl acetate/heptane (40/60) to give methyl 3-acetyl-1-butyl-1H-indole-6-carboxylate (3.38 g). MS (ESI+) for C16H19N1O3+H1 m/z 274.14 (M+H)+.

Source