Reaktion #1787621

Reaktionsgleichung

methanesulfonylchloride

sodium hydride

3-methyl-6-(2-methylphenyl)-4,5,6,7-tetrahydroindol-4-one

sodium hydrogen carbonate

methanesulfonylchloride

→

1-methanesulfonyl-3-methyl-6-(2-methylphenyl)-4,5,6,7-tetrahydroindol-4-one

Ausbeute 44.0%

Lösungsmittel

dimethylformamide

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at the same temperature for 12 hours
2. 2
   workup.STIRRINGthe mixture was stirred for 3 hours
3. 3
   Extraktionthe mixture was extracted with ethyl acetate
4. 4
   WaschenThe organic layer was washed with water and saturated brine
5. 5
   Trocknendried with magnesium sulfate
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   Sonstigethe residue was purified with silica gel column chromatography (EtOAc/hexane)
8. 8
   Sonstigeto give crystals, which
9. 9
   Sonstigewere recrystallized from ethyl acetate-hexane

Vorschrift

To a suspension of 60% sodium hydride (0.12 g, washed with hexane thrice) in dimethylformamide (10 ml) was added 3-methyl-6-(2-methylphenyl)-4,5,6,7-tetrahydroindol-4-one (0.60 g), and the mixture was stirred at room temperature for 30 minutes. To the mixture was added a solution of methanesulfonylchloride (0.43 g) in dimethylformamide (3 ml), and the mixture was stirred at the same temperature for 12 hours. To the mixture was added methanesulfonylchloride (0.74 g), and the mixture was stirred for 3 hours. To the mixture was added sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue was purified with silica gel column chromatography (EtOAc/hexane) to give crystals, which were recrystallized from ethyl acetate-hexane to give colorless crystals of 1-methanesulfonyl-3-methyl-6-(2-methylphenyl)-4,5,6,7-tetrahydroindol-4-one (0.35 g).

Quelle