Acetone → HCID 90386464, compound

Participants

Reaction Steps

To a solution of 3-bromo-5-(oxiran-2-yl)pyridine (1.00 g, 5.00 mmol) in acetone (25 mL) was added BF3.OEt2 (0.950 mL, 7.50 mmol) dropwise and the reaction mixture was stirred at ambient temperature for 14 h. The reaction mixture was diluted with water (15 mL) and the resulting mixture extracted with ethyl acetate (2×50 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give a residue which was purified by column chromatography using CombiFlash (REDISEP®, silica gel, 40 g, 25% EtOAc/hexanes) to obtain 3-bromo-5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridine (0.700 g, 54.2%). LCMS Condition B-26: retention time 2.17, [M+2]=260.0. 1H NMR (400 MHz, CDCl3) δ 1.48 (s, 3H), 1.55 (s, 3H), 3.72 (dd, J=7.6 Hz, J=8.4 Hz, 1H), 4.36 (dd, J=6.4 Hz, J=8.4 Hz, 1H), 5.08 (dd, J=6.4 Hz, J=7.6 Hz, 1H), 7.85-7.86 (m, 1H), 8.49 (d, J=1.6 Hz, 1H), 8.62 (d, J=2.0 Hz, 1H).

Provenance & Evidence