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

Participants

Role	Name	HCID	Charge
Reactant	2-Methylpyridine	HCID 7975	—
Reactant	2-{[6-(2-Chloro-4-methoxyphenoxy)hexyl]thio}-4,5-dihydrothiazol-4-one	HCID 18921835	—
Reactant	Butyllithium	HCID 178418339	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	2-[7-(2-Chloro-4-methoxyphenoxy)heptyl]pyridine	HCID 18921868	—

Reaction Conditions

Temperature	-78 °C

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

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05750532
Source dataset	uspto-grants-1998_05
ORD ID	ord-a5ec1fd6d723483f9cce9776a3b104ea
Source note	uspto-grants-1998_05