Trifluoroacetic acid → HCID 68780349, compound

Participants

Reaction Conditions

Reaction Steps

2-Pentanone (1 ml, 9.4 mmol) was dissolved in 15 ml of dry toluene in a two-neck flask, and the solution was cooled to 0° C. under argon. LiHMDS (9.4 ml, 1.0 M in THF, 2.1 mmol) was added via syringe with stirring, and the formed anion was allowed to sit for 1 min before the addition of butyryl chloride (0.49 ml, 4.7 mmol) in one portion with stirring. The flask was then removed from ice bath and allowed to stand for 1 min, and 1M HCl solution was added with stirring. The solution mixture was extracted with EtOAc. The organic mixture was then washed with brine, dried over Na2SO4, and evaporated under reduced pressure. To a solution of the resulting crude residue in toluene (20 ml) was added 4-amino-1,1,1-trifluoro-3-butene-2-one (0.72 g, 4.7 mmol) and trifluoroacetic acid (0.42 ml, 5.64 mmol) and the mixture was stirred under reflux for 24 h. The reaction mixture was washed with aq. 20% Na2CO3 and dried with Na2SO4. After removal of the solvent, the residue was submitted to silica gel column chromatography to give a title compound (0.62 g, 51%).

Provenance & Evidence