Reacción #792137

Ecuación de reacción

ethanone

1-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-2-[1,2,4]triazol-1-ylethanone

n-propylmagnesium chloride

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product

Rendimiento 36.0%

2-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-pentan-2-ol

Rendimiento 36.0%

Disolventes

dichloromethane

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThis mixture was then cooled to about 0° C.
2. 2
   workup.STIRRINGAfter stirring for about two hours
3. 3
   Temperaturato warm to room temperature
4. 4
   Otrowas then quenched by addition of a saturated ammonium chloride solution
5. 5
   ExtracciónThe organic components were extracted three times with DCM
6. 6
   Lavadowashed again with saturated ammonium chloride solution
7. 7
   Otrodried
8. 8
   Otrothe solvents evaporated
9. 9
   workup.ADDITIONAddition of diisopropyl ether
10. 10
    Otroresulted in precipitation of the
11. 11
    Filtraciónwas filtered off
12. 12
    OtroThe filtrate was then purified

Procedimiento

MgBr diethyl etherate (10.5 g, 40.2 mmol) was added to a solution of the above-mentioned ethanone (6.0 g, 16.8 mmol) in dichloromethane (DCM, 65 ml) and the mixture stirred at room temperature for about 90 min. This mixture was then cooled to about 0° C. and n-propylmagnesium chloride (22.8 ml of a 2 M solution in THF, 45.6 mmol) was added dropwise. After stirring for about two hours, the mixture was allowed to warm to room temperature and was then quenched by addition of a saturated ammonium chloride solution. The organic components were extracted three times with DCM, the organic phases combined, washed again with saturated ammonium chloride solution, dried and the solvents evaporated. Addition of diisopropyl ether resulted in precipitation of the unreacted starting material, which was filtered off. The filtrate was then purified using reverse phase chromatography, to give the product as a light brown colored solid (2.5 g, 36%, HPLC2 Rt=1.26 min, masse=392).

Fuente