[Cu][C:2]#N.C[Li].[Cl-].C([Al+]CC)C.[O:12]=[C:13]([C:21]1[CH:34]=[CH:33][C:24]2[N:25]=[C:26]([C:28]3[S:29][CH:30]=[CH:31][CH:32]=3)[O:27][C:23]=2[CH:22]=1)/[CH:14]=[CH:15]/[C:16]([O:18][CH2:19][CH3:20])=[O:17].[Cl-].[NH4+]>C1COCC1.CCCCCC>[CH3:2][CH:15]([CH2:14][C:13](=[O:12])[C:21]1[CH:34]=[CH:33][C:24]2[N:25]=[C:26]([C:28]3[S:29][CH:30]=[CH:31][CH:32]=3)[O:27][C:23]=2[CH:22]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17]
5 ml THF are added to 110 mg (1.23 mmol) copper-(I)-cyanide, the suspension is cooled to −5° C., then 770 μl (1.23 mmol) 1.6M methyl lithium dissolved in THF are added dropwise at a maximum temperature of 0° C., the mixture is stirred for 45 min, then cooled to −70° C. 1.23 ml (1.23 mmol) 1M diethyl aluminium chloride dissolved in hexane are then added dropwise to the reaction mixture, it is stirred for 25 min at −70° C., then are 100 mg (0.31 mmol) ethyl (E)-4-oxo-4-(2-thiophen-2-yl-benzoxazol-6-yl)-but-2-enoate dissolved in 5 ml THF are added dropwise. The reaction solution is then added to sat. ammonium chloride solution and extracted with diethyl ether. The org. phase is concentrated by rotary evaporation i. V. and the residue is purified by RP-HPLC.
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