Diisobutylaluminumhydride → 1-(Trifluoromethyl)cyclopropanemethanol

Temperature

0 °C

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)

1. customthe reaction was subsequently terminated by addition of 10 ml of methanol
2. 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. stirringstirred vigorously at room temperature overnight
4. customThe phases were separated
5. extractionthe aqueous phase was extracted three times with dichloromethane
6. dry with materialThe combined organic phases were dried over magnesium sulphate
7. filtrationfiltered
8. customthe solvent was removed under reduced pressure

ORD record

ord-bd86b2b2b4b94a849ac3e96ea4f9d0ad

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434690B2