Triphenylphosphine → HCID 20481559, compound

Participants

Reaction Steps

To a solution of 11.07 g (0.04 mole) of 1-(3-hydroxy-3-methyl-1-butyn-1-yl)-4-(2-diethylaminoethoxy)benzene and 8.4 g (0.04 mole) of 2-iodothiophene in 135 ml of triethylamine are added, under nitrogen, 4.95 g of pulverised potassium hydroxide. Then 310 mg of the palladium complex PdCl2 [P(C6H5)3 ]2 and 180 ml of copper(I) iodide are added and the reaction mixture is stirred for 20 hours at boiling temperature. The reaction mixture is taken up in 250 ml of ether and the solution is washed 3 times with 100 ml of water and once with saturated sodium chloride solution, dried over sodium sulfate and evaporated to dryness. The residue is chromatographed on silica gel with 96% of ether/4% of methanol (saturated with NH3), affording 9 g (75%) of 1-[4-(2-thienylethynyl)phenoxy]-2-diethylaminoethane in the form of a colourless oil with a refractive index of nD30 :1.6170.

Provenance & Evidence