[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[H-].[Na+].Br[CH2:20][CH2:21]Cl.O>CS(C)=O.C1COCC1.CCOCC>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([C:12]3([C:13]([O:15][CH3:16])=[O:14])[CH2:21][CH2:20]3)[CH:6]=[CH:7][CH:8]=2)[N:3]=1
To a solution of methyl 2-(2-methylquinolin-8-yl)acetate (0.78 g, 3.62 mmol) in DMSO (10 mL) and THF (5 mL) was added 60% NaH (0.72 g, 18.12 mmol) and the reaction mixture was stirred at ambient temperature for 30 minutes. 1-Bromo-2-chloroethane (0.90 mL, 10.87 mmol) was added slowly, and the reaction mixture was stirred at ambient temperature for 40 hours. Water (10 mL) and ether (50 mL) were added. The organic layer 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 methyl 1-(2-methylquinolin-8-yl)cyclopropanecarboxylate (0.416 g, 47.6%) as an oil.
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