Dimethylformamide → 3-Fluoro-2-pyridinecarboxaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of DABCO (8.8 g, 78.2 mmol) in anhydrous diethyl ether (250 mL) at −25° C. was added n-BuLi (1.6 M in hexanes, 49 mL, 78.2 mmol). The mixture was stirred between −25 to −10° C. for 45 min and then cooled to −70° C. To the above solution was added 3-fluoropyridine (5.9 mL, 71 mmol) dropwise. The reaction was stirred between −70 to −60° C. for 1.5 h before DMF (11.0 mL, 2.0 eq.) was added. After 1.0 h stirring at −70° C., water (150 mL) was added and warmed up to rt. The layers were separated and the aqueous layer was extracted with methylene chloride (5×100 mL). The combined organic layer was washed with brine and dried over Na2SO4. After removal of solvent, the crude was purified by silica gel column chromatography using gradient EtOAc in hexanes to give 5.4 g (55-60% yield) of 65A. 1H NMR (400 MHz, CDCl3) δ ppm 7.54-7.57 (m, 2H) 8.61 (d, J=2.20 Hz, 1H) 10.20 (s, 1H).

Provenance & Evidence