Iodine → HCID 67399749, compound

Participants

Reaction Conditions

Reaction Steps

A small amount of iodine was added to a suspension of 1-bromo-4-ethoxybenzene (484 μL) and magnesium (82.3 mg) in THF at room temperature in a nitrogen atmosphere, and the mixture was stirred at 50° C. for one hour. The reaction solution was returned to room temperature and a solution of 5-cyclopropyl-6-methoxypyridine-2-carbaldehyde (300 mg) in tetrahydrofuran (1 mL) was added, followed by stirring at 50° C. for one hour. Tetrahydrofuran was concentrated under reduced pressure and a saturated ammonium chloride solution was added, followed by extraction with ethyl acetate. The organic layer was filtered through diatomaceous earth, and then the solvent was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1→9:1) to give (5-cyclopropyl-6-methoxypyridin-2-yl)(4-ethoxyphenyl)methanol as a yellow oil (438 mg, 86%).

Provenance & Evidence