Reacción #40300

Ecuación de reacción

p-toluenesulphonyl chloride

2-tert-butylcyclohexanone

diisopropylamine

→

2-tert-butyl-6-chlorocyclohexanone

Rendimiento 81.0%

Disolventes

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAfter the addition
2. 2
   TemperaturaThe reaction mixture is heated to room temperature
3. 3
   Filtraciónfiltered with ether as eluant
4. 4
   ConcentraciónAfter concentration
5. 5
   Otroby evaporation in a vacuum 2-tert-butyl-6-chlorcyclohexanone (760 mg)
6. 6
   Otrois obtained in a yield of 81% (Tet. Lett. 1999, 40(12), 2231-2234)

Procedimiento

N-butyl lithium is added dropwise to a solution, cooled to 0° C., of diisopropylamine (5.5 mmol) in dry tetrahydrofuran. After the addition is complete the mixture is cooled to −78° C., and a solution of 2-tert-butylcyclohexanone (5 mmol) in dry tetrahydrofuran (50 ml) is introduced, followed by the addition of p-toluenesulphonyl chloride (5 mmol), also dissolved in dry tetrahydrofuran (50 ml). The reaction mixture is heated to room temperature and after stirring for 30 mins over silica gel filtered with ether as eluant. After concentration by evaporation in a vacuum 2-tert-butyl-6-chlorcyclohexanone (760 mg) is obtained in a yield of 81% (Tet. Lett. 1999, 40(12), 2231-2234).

Fuente