Réaction #40300

Équation de réaction

p-toluenesulphonyl chloride

2-tert-butylcyclohexanone

diisopropylamine

→

2-tert-butyl-6-chlorocyclohexanone

Rendement 81.0%

Solvants

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source