3-Chlorocyclopent-1-ene → 3-(5-Methoxyheptyl)cyclopent-1-ene

Participants

Reaction Conditions

Reaction Steps

A three-neck, round-bottomed flask containing magnesium metal turnings (7.2 g, 0.299 moles), is equipped with a Friedrich condenser and kept under a nitrogen atmosphere. Tetrahydrofuran (300 ml) is added and the contents are allowed to stir. A solution of 1-chloro-5-methoxyheptane (48.1 g, 0.292 moles) is added in small portions and refluxed. The mixture is allowed to stir for 3 hours. The resultant dark yellow solution is cooled to -25° C., and the condenser is removed and replaced with a dry ice addition funnel. A solution of 3-chlorocyclopentene (29.9 g, 0.292 moles) is added over a period of one hour. The viscous solution is poured into two liters of saturated ammonium chloride, extracted with ether, and dried over anhydrous sodium sulfate. Distillation yields 3-(5-methoxyheptyl)cyclopentene (51.5 g, 0.262 moles) as a clear, colorless oil boiling at about 90° C. at 0.3 mm and 54° C. at 0.1 mm.

Provenance & Evidence