Reaction #40300

Reaction equation

p-toluenesulphonyl chloride

2-tert-butylcyclohexanone

diisopropylamine

→

2-tert-butyl-6-chlorocyclohexanone

Yield 81.0%

Solvents

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

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

Procedure

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