Potassium Carbonate → 2-Bromo-3-[oxiranylmethoxy]pyridine

Participants

Reaction Steps

To a mixture of 25.2 g (0.145 mole) of 2-bromo-3-pyridinol and 30 g (0.22 mole) of potassium carbonate in 80 mL of N,N-dimethylformamide was added 30 g (0.13 mole) of (S)-glycidyl tosylate. The mixture was heated under nitrogen at 55–60° C. for 15 hours. The solvent was then removed in vacuum and replaced with 500 mL of methylene chloride, and the solution was washed with 500 mL of water and with saturated brine, dried over sodium sulfate, filtered and concentrated in vacuum. The residue was column chromatographed on silica gel with methylene chloride as eluant to give 17 g of the (S)-enantiomer of the title compound as a white solid. 1H-NMR (CDCl3): multiplet 8.01 δ (1H); multiplet 7.22 δ (2H); doublet of doublets 4.38 δ (1H); multiplet 4.04 δ (1H); multiplet 3.40 δ (1H); multiplet 2.95 δ (1H); multiplet 2.85 δ (1H).

Provenance & Evidence