Propargyl alcohol → (E)-6,6-dimethyl-4-hepten-2-yn-1-ol

Participants

Reaction Steps

0.63 g of (E)-1- iodo-3,3-dimethyl-1-butene [see J. Org. Chem., 43, 4424 (1978)] was dissolved in 10 ml of tetrahydrofuran, and 31 mg of triphenylphosphine, 29 mg of copper(I) iodide, 11 mg of palladium chloride, 1.5 ml of n-butylamine and 0.35 ml of propargyl alcohol were added. The mixture was stirred overnight at room temperature, and then water and ethyl acetate were added. The organic layer separated was worked up in a customary manner, and the product was purified by silica gel column chromatography [hexane/ethyl acetate=2/1] to give 0.27 g of the captioned compound as a pale brown oil.

Provenance & Evidence