反応 #40300

反応方程式

p-toluenesulphonyl chloride

2-tert-butylcyclohexanone

diisopropylamine

→

2-tert-butyl-6-chlorocyclohexanone

収率 81.0%

溶媒

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   workup.ADDITIONAfter the addition
2. 2
   温度The reaction mixture is heated to room temperature
3. 3
   ろ過filtered with ether as eluant
4. 4
   濃縮After concentration
5. 5
   その他by evaporation in a vacuum 2-tert-butyl-6-chlorcyclohexanone (760 mg)
6. 6
   その他is obtained in a yield of 81% (Tet. Lett. 1999, 40(12), 2231-2234)

実験手順

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).

出典