Hexane → HCID 131721846, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, a solution of n-butyllithium in hexane (24.0 ml; 1.6 mol/L; 38 mmol) was added dropwise to a cooled (0° C.) solution of di-(2-pentyl)cyclopentadiene (7.82 g; 38.0 mmol) in dry tetrahydrofuran (125 ml) in a 250 mL three-necked round-bottomed flask provided with a magnetic stirrer and a dropping funnel. After 24 hours of stirring at room temperature, 2-dimethylaminoethyl tosylate (38.0 mmol) prepared in situ was added. After 18 hours of stirring, the conversion was found to be 92%, and water (100 ml) was carefully added dropwise to the reaction mixture and the tetrahydrofuran was then distilled off. The crude product was extracted with ether, and the combined organic phase was then dried with sodium sulphate, and evaporated to dryness. The residue was purified on a silica gel column, which resulted in 8.2 g of (dimethylaminoethyl)-di(2-pentyl)cyclopentadiene.

Provenance & Evidence