2-Methylpyridine → 2-[7-(2-Chloro-4-methoxyphenoxy)heptyl]pyridine

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, add 152 mg. 2-picoline and 1.5 ml. tetrahydrofuran (THF) and cool to -28° C. Add 104 mg. n-butyl lithium and stir about 30 minutes at -78° C. Add 20 mg. of the iodide prepared in Examples 2 and 3 in 1 ml. THF. Stir 1 hour at -78° C., let warm to room temperature and stir about 15 hours. Work up with water and methylene chloride then wash with water and brine then dry over sodium sulfate. Elute on a coarse silica column with methylene chloride then 50% ethylacetate/methylene chloride to obtain the title compound. Prepare the hydrochloride salt by reaction of the title compound with 0.1N HCl.

Provenance & Evidence