Réaction #42501

Équation de réaction

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

Sodium hydroxide

Sodium hydroxide

→

3-acetyl-1-butyl-1H-indole-6-carboxylic acid

Rendement 84.3%

Solvants

methanol

Methanol

Conditions de réaction

Traitement

1. 1
   ConcentrationThe solution was concentrated to half its original volume and hydrochloric acid (2N)
2. 2
   workup.ADDITIONwas added until the aqueous layer
3. 3
   ExtractionThe mixture was extracted with dichloromethane
4. 4
   Lavagethe organic layer was washed with brine
5. 5
   Séchagedried over sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated
8. 8
   AutreThe resulting material was chromatographed on silica gel

Mode opératoire

Methyl 3-acetyl-1-butyl-1H-indole-6-carboxylate (2.00 g) was dissolved in methanol (100 mL). Sodium hydroxide (1N) was added until the mixture became slightly cloudy. Methanol was again added (20 mL) until the solution was clear. Sodium hydroxide was again added until the mixture was slightly cloudy. The mixture was allowed to stir at room temperature overnight. The solution was concentrated to half its original volume and hydrochloric acid (2N) was added until the aqueous layer indicated a pH of about one. The mixture was extracted with dichloromethane and the organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. The resulting material was chromatographed on silica gel using MeOH/heptane/dichloromethane (4/20/76) to give 3-acetyl-1-butyl-1H-indole-6-carboxylic acid (1.60 g). MS (ESI+) for Cl5H17N1O3+H1 m/z 260.13 (M+H)+.

Source