Reacción #40298

Ecuación de reacción

butyl lithium

cyclohex-2-enone

→

3-butylcyclohexanone

Disolventes

dimethyl sulphide

hexane

dimethyl sulphide

Condiciones de reacción

Tratamiento posterior

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
   Otrois quenched with saturated aqueous ammonium chloride solution
5. 5
   TemperaturaThe reaction mixture which has been heated to room temperature
6. 6
   Extracciónis extracted with diethyl ether
7. 7
   LavadoThe combined ether phases are washed with saturated aqueous ammonium chloride solution
8. 8
   Secadodried over sodium sulphate
9. 9
   OtroAfter evaporating-off of the solvent the residue obtained
10. 10
    Filtraciónthe solution is filtered
11. 11
    Concentraciónconcentrated by evaporation

Procedimiento

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).

Fuente