Réaction #42525

Équation de réaction

methyl 4-amino-5-butyryl-1-hydroxycyclohexa-2,4-diene-1-carboxylate

p-toluenesulfonic acid monohydrate

→

methyl 5-butyryl-1-hydroxy-4-oxocyclohex-2-ene-1-carboxylate

Solvants

water tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Autrepartitioned between dichloromethane and water
2. 2
   SéchageThe organic layer was dried (sodium sulfate)
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated under reduced pressure

Mode opératoire

To a stirred solution of methyl 4-amino-5-butyryl-1-hydroxycyclohexa-2,4-diene-1-carboxylate (1.25 g, 5.2 mmol) in a 1:1 mixture of water/tetrahydrofuran (10 mL) was added p-toluenesulfonic acid monohydrate (1.1 g, 5.8 mmol). The reaction mixture was stirred for 18 h and then partitioned between dichloromethane and water. The organic layer was dried (sodium sulfate), filtered, and concentrated under reduced pressure to afford methyl 5-butyryl-1-hydroxy-4-oxocyclohex-2-ene-1-carboxylate which was used without further purification or characterization.

Source