Acetonitrile → 5,5,5-Trifluoro-4,4-dimethyl-3-oxopentanenitrile

Temperature

-30 °C

To a mixture of acetonitrile (3.22 g, 44.1 mmol) in THF (60 mL) at −78° C. was added n-BuLi (17.63 mL, 44.1 mmol, 2.5 mol/L). The mixture was stirred at −30° C. for 0.5 h. Then to the mixture was added methyl 3,3,3-trifluoro-2,2-dimethylpropanoate (5 g, 29.4 mmol) dropwise. Then the mixture was stirred for another 1 h. The mixture was quenched with saturated NH4Cl solution (50 mL), extracted with EA (100 mL×2). The organic layer was dried over Na2SO4, filtered and concentrated to yield a crude product as a yellow oil of 5,5,5-trifluoro-4,4-dimethyl-3-oxopentanenitrile (3 g, 16.75 mmol, 57.0% yield): 1H NMR (400 MHz, CD3OD) δ 3.75 (s, 2H), 1.40 (s., 6H).

1. stirringThen the mixture was stirred for another 1 h
2. customThe mixture was quenched with saturated NH4Cl solution (50 mL)
3. extractionextracted with EA (100 mL×2)
4. dry with materialThe organic layer was dried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated

ORD record

ord-46becf7e1889445699bbc46b49da77bf

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382238B2