2-Methyl-3-butyn-2-ol → 4-(4-Cyanophenyl)-2-methyl-3-butyne-2-ol

Participants

Reaction Steps

30 g of 4-bromobenzonitrile, 13.4 g of 3-methyl-1-butyn-3-ol, 0.7 g of triphenylphosphine and 0.3 g of bis(triphenylphosphine) palladium(II) chloride were dissolved in 140 ml of triethylamine in nitrogen atmosphere, and 0.1 g of copper(I) iodide was added thereto. This was stirred for one hour at room temperature and then for 5 hours at 90° C. The crystals as precipitated were filtered out and, after triethylamine was removed by distillation, extracted with chloroform. The crystals were washed two times with 10% hydrochloric acid and two times with water, and chloroform was removed by distillation. The residue was distilled under reduced pressure (b.p. 140° to 160° C./5 mmHg) to obtain 23.5 g of 3-methyl-1-(4'-cyanophenyl)-1-butyn-3-ol.

Provenance & Evidence