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

Temperature

-78 °C

To a mixture of MeCN (13.9 mL, 264 mmol) in THF (500 mL) cooled to −78° C. was added n-BuLi (106 mL, 264 mmol). 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 (30 g, 176 mmol) dropwise. The mixture was stirred at 25° C. for 10 h. The mixture was quenched with aqueous NH4Cl (50 mL), extracted with EA (300 mL×3). The organic layer was dried over Na2SO4, filtered and concentrated to yield a crude product of a yellow oil of 5,5,5-trifluoro-4,4-dimethyl-3-oxopentanenitrile (22 g, 122.9 mmol, 70% yield): 1H NMR (400 MHz, CDCl3) δ 3.75 (s, 2H), 1.41 (s, 6H).

1. stirringThe mixture was stirred at 25° C. for 10 h
2. customThe mixture was quenched with aqueous NH4Cl (50 mL)
3. extractionextracted with EA (300 mL×3)
4. dry with materialThe organic layer was dried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated

ORD record

ord-c9e530d69b824e5face4131d9704de74

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382238B2