Diethyl Ether → HCID 178506815, compound

Participants

Reaction Steps

Ten mL (85.7 mmol) of indene, which is a cyclopentacarbyl compound, was added to a container that contained 150 mL of diethyl ether and 15 mL of tetrahydrofuran to form a first mixture. This first mixture was then reacted with 53.6 mL (85.7 mmol) of n-butyllithium (1.6 M in hexane) to form indenyllithium, which is a cyclopentacarbyl metal compound. This reaction took place at −78° C. A yellow solution was formed. This yellow solution was then stirred at room temperature (about 25° C.) for four hours and then cooled again to −78° C. An equivalent quantity of 1-bromohexene, a haloalkene compound, was added dropwise to the yellow solution to form a second mixture. This second mixture was then stirred overnight at room temperature (about 25° C.). Thereafter, this second mixture was then hydrolyzed with 50 mL of water to form an organic phase and a water phase. The organic phase was dried over sodium sulfate and then the solvent was evaporated under a vacuum to produce a third mixture. This third mixture was then distilled using a high vacuum (10−2 torr) to obtain a product. The product obtained was 5-hexenyl-1-indene, which is an ((omega-alkenyl) cyclopentacarbyl) compound.

Provenance & Evidence