Réaction #1102625

Équation de réaction

methyl 1-benzyl-3-methylindoline-5-carboxylate

o-chloranil

→

methyl 1-benzyl-3-methyl-1H-indole-5-carboxylate

Solvants

tert-butyl methyl ether

Conditions de réaction

Traitement

1. 1
   LavageAfter dilution with ethyl acetate and subsequent washing with a 1 M sodium hydroxide aqueous solution, it
2. 2
   Séchagewas dried over anhydrous sodium sulfate
3. 3
   AutreAfter evaporation of the solvent
4. 4
   Autrethe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:30 to 1:20 to 1:10)

Mode opératoire

A 269 mg portion of methyl 1-benzyl-3-methylindoline-5-carboxylate was dissolved in 10 ml of tert-butyl methyl ether, and 235 mg of o-chloranil was added, followed by stirring at room temperature for 1 hour. After dilution with ethyl acetate and subsequent washing with a 1 M sodium hydroxide aqueous solution, it was dried over anhydrous sodium sulfate. After evaporation of the solvent, the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:30 to 1:20 to 1:10) to obtain 433 mg of methyl 1-benzyl-3-methyl-1H-indole-5-carboxylate as a colorless solid.

Source