Pyridine → HCID 178445656, compound

Participants

Reaction Steps

26 g of 4-bromophenol, 100 ml of dimethylformamide, and 13 g of pyridine were dissolved. 31 g of commercially available trans-4-n-butylcyclohexane carboxylic acid chloride was added dropwise to the solution and the mixture was heated while stirring. The reaction mixture was poured into water to produce crystals. The crystals were collected by filtration, washed with dilute HCl and then water, dried in vacuum, and recrystallized from a mixed solvent of ethyl acetate and methanol to obtain 44 g of 4-bromophenyl trans-4-n-butylcyclohexane carboxylate. To this were added 20 g of 4-ethoxyphenyl acetylene, 0.09 g of bis(triphenylphosphine)-palladium(II) chloride, 0.1 g of copper iodide, 0.79 g of triphenylphosphine, and 260 ml of triethylamine, and the mixture was heated while stirring. After the reaction, the reaction product was poured into water and neutralized with HCl to produce crystals. The crystals were collected by filtration, washed with water, dried in vacuum, and recrystallized from a mixed solvent of ethyl acetate and methanol to obtain 40 g of a compound having the following formula. ##STR43##

Provenance & Evidence