Potassium Iodide → 5-(2-acetyl-phenoxy)-4-chloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one

Participants

Reaction Conditions

Reaction Steps

A solution of 4,5-dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one (Intermediate 20, 60.0 g, 0.24 mol) in acetone (600 mL) was treated with potassium carbonate (28.4 g, 0.21 mol), tetrabutylammonium bromide (1.2 g), potassium iodide (38.4 g, 0.23 mol) and 1-(2-hydroxy-phenyl)-ethanone (38.4 g, 0.28 mol). The resulting reaction mixture was stirred at 25° C. for 120 h. After this time, the reaction was filtered. The filtrate was concentrated in vacuo. Silica gel column chromatography (1:10 ethyl acetate/petroleum ether) afforded 5-(2-acetyl-phenoxy)-4-chloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one (15 g, 18%).

Provenance & Evidence