Triethylamine → 4,4,5,5,5-pentafluoro-N-methoxy-N-methylpentanamide

Participants

Reaction Conditions

Reaction Steps

Triethylamine (1.082 mL, 7.81 mmol) was added to a stirred solution of 4,4,5,5,5-pentafluoropentanoic acid (1.00 g, 5.21 mmol), N,O-dimethylhydroxylamine hydrochloride (0.559 g, 5.73 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.998 g, 5.21 mmol) in dry DCM (5.35 mL) at 25° C. under N2. The reaction was stirred at 25° C. overnight. The reaction was diluted with CH2Cl2 (60 mL) and washed consecutively with 1N aq. HCl (2×), satd aq. NaHCO3, dried (Na2SO4) and concentrated in vacuo to give the desired product, as a colorless liquid. 1H NMR (500 MHz, CHCl3-d): δ 3.72 (s, 3H); 3.21 (s, 3H); 2.74 (t, J=7.8 Hz, 2H); 2.51-2.37 (m, 2H). m/z=236.2 (M+H).

Provenance & Evidence