反应 #40298

反应方程式

butyl lithium

cyclohex-2-enone

→

3-butylcyclohexanone

溶剂

dimethyl sulphide

hexane

dimethyl sulphide

反应条件

后处理

1. 1
   workup.STIRRINGstirred for a further 5 to 15 mins
2. 2
   workup.ADDITIONis slowly added dropwise
3. 3
   workup.STIRRINGAfter stirring for one hour at −78° C. the mixture
4. 4
   其他is quenched with saturated aqueous ammonium chloride solution
5. 5
   温度The reaction mixture which has been heated to room temperature
6. 6
   萃取is extracted with diethyl ether
7. 7
   洗涤The combined ether phases are washed with saturated aqueous ammonium chloride solution
8. 8
   干燥dried over sodium sulphate
9. 9
   其他After evaporating-off of the solvent the residue obtained
10. 10
    过滤the solution is filtered
11. 11
    浓缩concentrated by evaporation

实验过程

A solution of copper iodide (6.3 mmol) in dimethyl sulphide (12 ml) is cooled to 50° C. A solution of butyl lithium (6.2 mmol) is added dropwise accompanied by stirring and stirred for a further 5 to 15 mins. The reaction mixture is cooled to −78° C. and then a solution precooled to −78° C. of cyclohex-2-enone (6 mmol), dissolved in dimethyl sulphide (1 ml), is slowly added dropwise. After stirring for one hour at −78° C. the mixture is quenched with saturated aqueous ammonium chloride solution. The reaction mixture which has been heated to room temperature is extracted with diethyl ether. The combined ether phases are washed with saturated aqueous ammonium chloride solution and dried over sodium sulphate. After evaporating-off of the solvent the residue obtained is taken up in hexane, the solution is filtered and concentrated by evaporation. After chromatography of the residue on silica gel with ethyl acetate/hexane 1:4 pure 3-butylcyclohexanone is obtained (Tetrahedron 1989, 45 (2), 425-434).

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