Hydrochloric Acid → HCID 22241648, compound

Participants

Reaction Conditions

Reaction Steps

Under Ar(g), a solution of anhydrous acetonitrile (0.506 mL) in 25 mL anhydrous THF is cooled to −78° C. in a dry ice-acetone bath and then treated in dropwise fashion with 6.0 mL of a 1.6 M n-butyl lithium in hexanes. The reaction mixture is maintained at −78° C. for an additional 1 h and subsequently treated in dropwise fashion with a solution of 5 gms. of (2,4,6-trimethyl-phenyl)-acetic acid ethyl ester in 25 mL of anhydrous THF. The resulting solution is then stirred 5 h at room temperature. Subsequently, the reaction mixture is acidified (pH 7-8) with dropwise addition of conc. HCl and a 1 M HCl(aq) solution. The quenched reaction mixture is then partitioned between water and ethyl acetate. The organic layer is dried over anhydrous Na2SO4, filtered and concentrated in vacuo to yield the desired 3-oxo-4-(2,4,6-trimethyl-phenyl)-butyronitrile as a yellow-white solid in the amount of 1.41 gms. (72% yield).

Provenance & Evidence