[Li][CH3:2].C[Si](Cl)(C)C.[CH3:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[C:12](/[C:19](/[CH3:26])=[CH:20]\[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:13]=[CH:14][CH:15]=2)[N:10]=1>CCOCC.C(Cl)Cl>[CH3:26][C:19]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[N:10]=[C:9]([CH3:8])[CH:18]=[CH:17]2)([CH3:2])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]To a mixture of Cu(I)I (2.42 g, 12.7 mmol) in ether (5 mL) was added a solution of 1.6 M MeLi (15.9 ml, 25.4 mmol) in ether at 0° C. and the mixture was stirred at 0° C. for 10 minutes. The solvent was removed under reduced pressure and cold DCM (10 mL) was added. The solvent was removed under reduced pressure. Cold DCM (40 mL) was added and the mixture was cooled to −78° C. TMSCl (1.54 mL, 12.7 mmol) was added, followed by a solution of (Z)-ethyl 3-(2-methylquinolin-8-yl)but-2-enoate (0.81 g, 3.17 mmol) in DCM (10 mL). The reaction mixture was warmed to 0° C. and stirred at 0° C. for 1 hour. The reaction mixture was quenched with saturated ammonium chloride solution. The organic layers was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (7:1 hexane/ethyl acetate) to give ethyl 3-methyl-3-(2-methylquinolin-8-yl)butanoate (0.66 g, 76.8%) as an oil.
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