Reacción #85154

Ecuación de reacción

diisobutylaluminum hydride

methyl 1-(trifluoromethyl)cyclopropanecarboxylate

→

[1-(Trifluoromethyl)cyclopropyl]methanol

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe reaction was subsequently terminated by addition of 10 ml of methanol
2. 2
   workup.ADDITIONThe reaction mixture was diluted with 30 ml of aqueous 20% strength sodium potassium tartrate solution and 30 ml of aqueous buffer solution (pH 7)
3. 3
   workup.STIRRINGstirred vigorously at room temperature overnight
4. 4
   OtroThe phases were separated
5. 5
   Extracciónthe aqueous phase was extracted three times with dichloromethane
6. 6
   SecadoThe combined organic phases were dried over magnesium sulphate
7. 7
   Filtraciónfiltered
8. 8
   Otrothe solvent was removed under reduced pressure

Procedimiento

At 0° C., 26.7 ml (26.7 mmol) of diisobutylaluminum hydride (1M in dichloromethane) were slowly added dropwise to a solution of 1.89 g (10.7 mmol) of methyl 1-(trifluoromethyl)cyclopropanecarboxylate in 10 ml of dichloromethane. The mixture was then stirred at 0° C. for another 2 h and the reaction was subsequently terminated by addition of 10 ml of methanol. The reaction mixture was diluted with 30 ml of aqueous 20% strength sodium potassium tartrate solution and 30 ml of aqueous buffer solution (pH 7) and stirred vigorously at room temperature overnight. The phases were separated and the aqueous phase was extracted three times with dichloromethane. The combined organic phases were dried over magnesium sulphate and filtered, and the solvent was removed under reduced pressure. The crude product corresponded to the title compound. Yield: 0.96 g (64% of theory)

Fuente