2-Methyl-3-butyn-2-ol → 2-Methyl-4-(4-propylphenyl)-3-butyn-2-ol

Participants

Reaction Conditions

Reaction Steps

60 g of 1-bromo-4-propylbenzene, 38 g of 3-methyl-1-butyn-3-ol, 1.3 g of triphenylphosphine and 0.7 g of bis(triphenylphosphine) palladium(II) chloride were dissolved in 260 ml of triethylamine in nitrogen atmosphere, and 0.2 g of copper(I) iodide was added thereto. This was stirred for one hour at room temperature and for 5 hours at 90° C. The crystals as precipitated were filtered out and, after triethylamine was removed by distillation, extracted with chloroform. These were washed two times with 10% hydrochloric acid and two times with water, and chloroform was removed by distillation. The residue was purified by silicagel-chloroform column chromatography to obtain 37 g of 3-methyl-1-(4'-propylphenyl)-1-butyn-3-ol.

Provenance & Evidence