Реакция #40300

Уравнение реакции

p-toluenesulphonyl chloride

2-tert-butylcyclohexanone

diisopropylamine

→

2-tert-butyl-6-chlorocyclohexanone

Выход 81.0%

Растворители

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Условия реакции

Обработка

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

Методика

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).

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