N,N-Diallyl-2,2,2-trifluoroacetamide → 1-(trifluoroacetyl)-2,5-dihydro-1H-pyrrole

Participants

Reaction Steps

To a stirred solution of 319 (26.9 mmol) in freshly distilled CH2Cl2 (250 mL), under nitrogen (1 atm) was added Grubb's Catalyst {RuCl2(CHC6H5)[P(C6H11)2], 0.5 mol %}. After 1.5 h stirring at room temperature, TLC indicated complete conversion of the starting material to a more polar product. The reaction was quenched by bubbling air through the solution. The solution was concentrated and subjected to chromatography purification (5–20% EtOAc in hexanes) to yield 1-(2,5-dihydro-pyrrol-1-yl)-2,2,2-trifluoro-ethanone (320) (22.0 mmol, 82% yield).

Provenance & Evidence