Triethylamine → Methyltriethylammonium 3-cyanotetrafluoropropionate

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Reaction Steps

A homogeneous solution of 9.3 g (0.05 mole) of methyl 3-cyanotetrafluoropropionate prepared as in Example 3, and 5.1 g (0.05 mole) of triethylamine in 25 ml of ether was stirred at 25°. After 4 days, a second layer had slowly formed; no increase was observed during an additional 2 days. Removal of volatiles under full pump at 25° gave a deliquescent yellow solid, methyltriethylammonium-3-cyanotetrafluoropropionate, mp 52°-55°. IR (CDCl3): 2965 (sat'd CH), 2255 (CN), 1690 (CO2), and 1250-1100 cm-1 (CF). NMR (CDCl3): 1H 3.47 (q, JHH 7.1 Hz, 6H, CH2 --N, 3.08 (s, 3H, CH3 --N), and 1.37 ppm (t, JHH 7.1 Hz, of m, 9H, CH3); 19F -108.5 (t, JFF 8.4 Hz, 2 F, CF2CN) and -119.3 ppm (t, JFF 8.4 Hz, 2F, CF2C=O with only 3% of impurities present.

Provenance & Evidence