Isopropyl iodide → 3-Isopropyloxypyridine

Participants

Reaction Steps

5-bromo-1H-pyridone 1BI (100 g, 0.58 mol), potassium carbonate (238 g, 1.73 mol) and 2-iodopropane (86 ml, 0.86 mol) were stirred in DMF (1 L) at r.t. for 1 day. The mixture were diluted with ethyl acetate and water, layers were separated. The separated organic layer was washed with water (×2), dried (Mg SO4) and filtered. Solvents were removed in vacuum and column purification [5% ethyl acetate in hexanes] gave first the less polar 5-isopropoxypyridine 2BIa (73 g, 59%) as colourless liquid. Continuous elution with [50% ethyl acetate in hexanes] gave the more polar 5-bromo-1-isopropylpyridone 2BIb as white solid (22 g, 18%).

Provenance & Evidence