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

Participants

Reaction Conditions

Reaction Steps

To a mixture of MeCN (1.086 g, 26.5 mmol) in THF (300 mL) cooled to −78° C. was added n-BuLi (10.58 mL, 26.5 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 (3 g, 17.63 mmol) dropwise. The mixture was quenched with aqueous NH4Cl and extracted with DCM/MeOH (10:1, 30 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was purified by silica column chromatography (PE/EA=8:1). All fractions found to contain product by TLC (PE/EA=5:1, Rf=0.5) were combined and concentrated to yield a light yellow oil of 5,5,5-trifluoro-4,4-dimethyl-3-oxopentanenitrile (1 g, 5.30 mmol, 30% yield): 1H NMR (400 MHz, CDCl3) δ 3.79 (s, 2H), 1.41 (s, 6H).

Provenance & Evidence