Hydroxy-1-propyne (48 mg) was dissolved in benzene (1 ml). 5-Iodo-2,2'-bithiophene (0.1 g) was added immediately and stirred. A mixture of CuI (0.05 g), benzyltriethylammonium chloride (0.05 g), catalyst Pd(PPh3)4 (0.1 g) and 3 ml of NaOH solution (2.5N) were mixed together at room temperature and stirred for 2 hours. NH4Cl solution (4 ml) was then added. The reaction solution was extracted with ethyl acetate. The extract was washed with 10 ml of HCl (10%) for 3 times, 50 ml of water twice and dried over anhydrous magnesium sulfate. The residual solid was purified by silica gel column chromatography, eluted with ethyl acetate/n-hexane (3/1) to yield 56 mg of the product (74%).
