Hydrochloric Acid → HCID 59408349, compound

Participants

Reaction Steps

8.0 g (22.0 mmol) of 4′-(4-bromophenyl)-4-propylbicyclohexyl are stirred at 60° C. for 60 h in 80 ml of NEt3 together with 4.4 ml (44.0 mmol) of 1-pentyne in the presence of 309 mg (0.44 mmol) of bis(triphenylphosphine)palladium(II) chloride and 42 mg (0.22 mmol) of copper(I) iodide. The batch is added to ice-water and acidified using hydrochloric acid. The mixture is extracted with MTBE, and the combined organic phases are washed with water and sat. sodium chloride solution. The solution is concentrated to completion, and the crude product is purified by column chromatography (SiO2, n-heptane). The further purification is carried out by recrystallisation from n-heptane (−20° C.). This gives 4′-(4-pent-1-ynylphenyl)-4-propylbicyclohexyl as a colourless solid (m.p. 47° C.).

Provenance & Evidence