[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([C:14]3[S:15][CH:16]=[CH:17][CH:18]=3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.O1CCC[CH2:20]1.C([Li])CCC.COS(OC)(=O)=O>C([Li])CCC.O>[CH3:20][C:16]1[S:15][C:14]([C:12]2[S:13][C:9]([C:6]3[CH:5]=[CH:4][C:3]([S:2][CH3:1])=[CH:8][CH:7]=3)=[CH:10][CH:11]=2)=[CH:18][CH:17]=1Under a nitrogen atmosphere, a stirred solution of 0.82 gram (0.003 mole) of 5-(4-methylthiophenyl)[2,2'-bithienyl] in 100 ml of freshly distilled tetrahydrofuran was cooled to 0° C. and 1.4 ml of n-butyllithium (2.6M in hexanes) was added dropwise via syringe during a ten minute period. Upon completion of addition the reaction mixture stirred at 0° C. for 30 minutes, then at ambient temperature for three hours. The reaction mixture was recooled to 0° C. and an additional five drops of n-butyllithium was added. The reaction mixture stirred at 0° C. for one hour then 0.32 ml (0.0034 mole) of dimethylsulfate was added. Upon completion of addition the reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was taken up in 70 ml of water and the organic layer was separated. The aqueous layer was washed with three 25 ml portions of chloroform. The organic layers were combined and washed, first with water, then with an aqueous solution saturated with sodium chloride. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to yield 0.78 gram of 5'-methyl-5-(4-methylthiophenyl)[2,2'-bithienyl]; m.p. 145°-147° C.
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