Hexane → HCID 18322221, compound

Participants

Reaction Conditions

Reaction Steps

0.69 g (3.55 mmol) of 4-bromopyridine hydrochloride was initially converted into the free base. To this end, the salt was dissolved in 5 ml of 1 M aqueous sodium hydroxide solution, the solution was extracted three times with diethyl ether and the combined organic phases were dried and evaporated to dryness using a rotary evaporator. The residue was dissolved in 5 ml of absolute diethyl ether and the solution was added dropwise at −70° C. to a mixture of 1.6 M butyllithium solution in n-hexane (3.98 mmol) and 10 ml of absolute diethyl ether. The mixture was stirred at −70° C. for 30 min, and a solution of 0.5 g (1.78 mmol) of N-(2-(3-methoxyphenyl)ethyl)phthalimide in 10 ml of absolute tetrahydrofuran was then added dropwise (color change from yellow to brown). After 1 h, the reaction mixture was allowed to warm to room temperature, admixed with 10 ml of saturated ammonium chloride solution and extracted three times with diethyl ether. The combined organic phases were washed once with saturated sodium chloride solution, dried and evaporated to dryness using a rotary evaporator. Recrystallization of the crystalline residue from diisopropyl ether/ethanol gave a colorless crystalline product. Yield: 0.28 g. M.p.: 190° C.

Provenance & Evidence