2,3-Dimethyl-1,3-butadiene → 4-(4,5-Dimethylcyclohexa-1,4-dienyl)butan-1-ol

Participants

Reaction Conditions

Reaction Steps

800 mg (2.00 mmol) of 1,2-bis(diphenylphosphino)ethane, 437 mg (2.00 mmol) of cobalt bromide, 1.28 g (4.00 mmol) of zinc iodide, and 260 mg (4.00 mmol) of zinc were added to 40 ml of THF, and the solution was stirred for 15 minutes at 70° C. The solution was cooled to room temperature, and 9.86 g (120 mmol) of 2,3-dimethyl-1,3-butadiene was added thereto. Subsequently, 9.8 g (100 mmol) of 5-hexyn-1-ol was slowly added dropwise to the mixture in a water bath. The resulting mixture was stirred for one hour at 35° C., and then the solvent was distilled off under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane/ethyl acetate=3/1), and thus 11.5 g of the title compound alcohol was obtained as a colorless oil. Yield 63.4%.

Provenance & Evidence