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 at ambient temperature and the reaction mixture was stirred for 14 h. The reaction mixture was diluted with water (15 mL) and extracted with EtOAc (2×50 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The resulting residue was purified by 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%) as a pale yellow liquid. LCMS (Condition 8): retention time 2.17 min, [M+2]=260.0. 1H NMR (400 MHz, CDCl3) δ 1.48 (s, 3 H), 1.55 (s, 3 H), 3.72 (dd, J=7.6 Hz, J=8.4 Hz, 1 H), 4.36 (dd, J=6.4 Hz, J=8.4 Hz, 1 H), 5.08 (dd, J=6.4 Hz, J=7.6 Hz, 1 H), 7.85-7.86 (m, 1 H), 8.49 (d, J=1.6 Hz, 1 H), 8.62 (d, J=2.0 Hz, 1 H).

Provenance & Evidence