Stannane, tributyl(1-ethoxyethenyl)- → 1-(5-Fluoropyridin-2-yl)ethan-1-one

Participants

Reaction Conditions

Reaction Steps

Copper iodide (811 mg), 1-ethoxyvinyltri-n-butyltin (19.2 mL), and bis(triphenylphosphine)palladium (II) chloride (1 g) were added to a solution of 2-bromo-5-fluoropyridine (5 g) in acetonitrile (250 mL), and the reaction solution was heated and stirred in a nitrogen atmosphere at 100° C. for two hours. The reaction solution was returned to room temperature, and the solvent was evaporated under reduced pressure. The residue was diluted with ethyl acetate and washed with brine. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was diluted with acetone (120 mL), and (1S)-(+)-10-camphorsulfonic acid (9.9 g) was added to the reaction solution. After confirming production of the target product by thin-layer chromatography, the solvent was evaporated under reduced pressure. The residue was diluted with an ether and neutralized with sodium carbonate. Water was added to the reaction solution, and the organic solution was separated. The organic layer was dried over magnesium sulfate, and the residue was purified by silica gel column chromatography (carrier: Chromatorex; elution solvent: hexane-ethyl acetate) to obtain 3.55 g of the title compound. The property values of the compound are as follows.

Provenance & Evidence