Reaktion #792137

Reaktionsgleichung

ethanone

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

n-propylmagnesium chloride

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product

Ausbeute 36.0%

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

Ausbeute 36.0%

Lösungsmittel

dichloromethane

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThis mixture was then cooled to about 0° C.
2. 2
   workup.STIRRINGAfter stirring for about two hours
3. 3
   Temperaturto warm to room temperature
4. 4
   Sonstigewas then quenched by addition of a saturated ammonium chloride solution
5. 5
   ExtraktionThe organic components were extracted three times with DCM
6. 6
   Waschenwashed again with saturated ammonium chloride solution
7. 7
   Sonstigedried
8. 8
   Sonstigethe solvents evaporated
9. 9
   workup.ADDITIONAddition of diisopropyl ether
10. 10
    Sonstigeresulted in precipitation of the
11. 11
    Filtrationwas filtered off
12. 12
    SonstigeThe filtrate was then purified

Vorschrift

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).

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