Hydrochloric Acid → 1-Decen-4-yne

Participants

Reaction Steps

A solution of bromoethane (43.6 g, 400 mmol) in Et2O (280 ml) was added dropwise to a suspension of Mg (9.6 g, 400 mmol) in Et2O (140 ml). After 3 hours a solution of 1-heptyne (35.0 g, 360 mmol) in Et2O (140 ml) was added dropwise to the reaction medium. After 90 minutes at reflux, CuCl (1.8 g, 18.2 mmol) was added to the cold reaction mixture and after 15 minutes a solution of allyl bromide (48.4 g, 400 mmol) in Et2O (140 ml) was added dropwise. After 18 hours at reflux, the cold reaction mixture was poured onto 10% aqueous HCl (320 ml) at 0° C. The aqueous phase was extracted with Et2O, then the organic phase was washed with H2O, dried (MgSO4), concentrated and distilled through a Vigreux column (65°/15 mbar) to afford the pure desired compound (70%).

Provenance & Evidence