Ethyl trifluoroacetate → 2,2,2-trifluoro-N-(prop-2-yn-1-yl)acetamide

Participants

Reaction Conditions

Reaction Steps

This compound has been prepared using a literature method (K. A. Cruickshank, D. L. Stockwell (1988) Tetrahedron Lett. 29, 5221). Propargylamine (90.9 mmol, 5 g, 6.227 mL) was added to methanol (90 mL) and the solution cooled to 0° C. Ethyl trifluoroacetate (1.3 equiv., 118.2 mmol, 16.8 g, 14.1 mL) was added and the mixture stirred at room temperature for 24 h. The solvent was evaporated, the residue diluted with 90 mL chloroform and washed with aqueous NaHCO3 solution (2×75 mL) and water (1×75 mL). The organic layer was evaporated and the orange residue distilled in vacuum to give N-propargyltrifluoroacetamide (13.171 g, 96%) as a colorless liquid which solidifies at −20° C. bp: 41° C./1.5 mm (bp ref.: 51° C./2.5 mm), mp: 31-33° C. 1H-NMR (CDCl3): 2.34 (m, 1H, CH), 4.15 (dd, 2H, CH2), 7.80 (br s, H, NH). 1H-NMR (CDCl3): 2.34 (t, 1H), 4.16 (dd, 2H), 7.00 (br s, 1H). 13C-NMR (CDCl3): 29.4 (CH2), 72.4 (CH), 77.0 (C), 109.859, 113.673, 117.470, 121.276 (CF3, J=286.37 Hz), 156.748, 157.249, 157.750, 158.250 (CO, J=37.77 Hz).

Provenance & Evidence