Реакция #792137

Уравнение реакции

ethanone

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

n-propylmagnesium chloride

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product

Выход 36.0%

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

Выход 36.0%

Растворители

dichloromethane

THF

Условия реакции

Обработка

1. 1
   ТемператураThis mixture was then cooled to about 0° C.
2. 2
   workup.STIRRINGAfter stirring for about two hours
3. 3
   Температураto warm to room temperature
4. 4
   Другоеwas then quenched by addition of a saturated ammonium chloride solution
5. 5
   ЭкстракцияThe organic components were extracted three times with DCM
6. 6
   Промывкаwashed again with saturated ammonium chloride solution
7. 7
   Другоеdried
8. 8
   Другоеthe solvents evaporated
9. 9
   workup.ADDITIONAddition of diisopropyl ether
10. 10
    Другоеresulted in precipitation of the
11. 11
    Фильтрацияwas filtered off
12. 12
    ДругоеThe filtrate was then purified

Методика

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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