To a 100 mL Schlenk flask were added 0.5 mL of diisopropyl amine and 20 mL of dry THF. The flask was cooled to −78° C. 3.5 mmol of n-butyl lithium in hexane was then added to the above solution. The mixture was stirred at −78° C. for 30 minutes. After stirring, 1.0 g of tetradecylthiophene-3-carboxylate in 10 mL THF was added dropwise to the solution. After stirring at −78° C. for another 2 hours, 0.7 mL of DMF was syringed into the reaction mixture. The reaction mixture was stirred for 5 h at −78° C. and 1 mL of acetic acid was added to the flask. The mixture was poured into a separation funnel and diethyl ether was added to the mixture. The organic layer was washed 3 times with 100 mL of water, dried with MgSO4, and the solvents were removed by rotary evaporation. The resulting residue was purified by column chromatography using a mixture of hexane and dichloromethane to give the desired compound. The NMR data were obtained and were consistent with those of the desired compound.
