Perfluoro-1-butanesulfonyl fluoride → 2-Pyrazinecarboxylic acid, 5-(fluoromethyl)-, methyl ester

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Reaction Conditions

Reaction Steps

To a solution of methyl 5-(hydroxymethyl)pyrazine-2-carboxylate (0.64 g) in THF (20 mL) was added triethylamine (2.30 g) and the solution was cooled to 0° C. Triethylamine trihydrofluoride (1.22 g) was then added followed by nonafluorobutanesulfonyl fluoride (2.28 g) dropwise over 5 mins. After warming to RT and stirring for 2 h, NaHCO3 (sat., aq., 100 mL) was added, and the mixture was extracted with EtOAc (2×50 mL). The combined organic portions were dried over MgSO4, evaporated, and purified by silica gel chromatography (5% to 50% EtOAc in hexane) to afford the title compound (94 mg). 1H NMR (400 MHz, CDCl3) δ ppm 4.07 (s, 3 H), 5.67 (d, J=46.5 Hz, 2 H), 8.89 (s, 1 H), 9.28 (s, 1 H)

Provenance & Evidence