[Cl:1][C:2]1[C:3]([CH3:15])=[C:4]([CH:12]=[CH:13][CH:14]=1)[NH:5][C:6](=[O:11])[C:7]([CH3:10])([CH3:9])[CH3:8].[CH2:16]([Li])[CH2:17][CH2:18]C.ICCC>C1COCC1.CCCCCC.O>[CH2:15]([C:3]1[C:2]([Cl:1])=[CH:14][CH:13]=[CH:12][C:4]=1[NH:5][C:6](=[O:11])[C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:16][CH2:17][CH3:18]
A solution of 3-chloro-N-(2,2-dimethylpropionyl)-2-methylaniline (9.79 g) in dry THF (150 ml) was stirred under nitrogen at 0° while a solution of n-butyllithium in hexane was added in a dropwise fashion until a slight orange color was noted. The volume of n-butyllithium solution which had been added was noted, and an equal volume of this n-butyllithium solution was then added in order to complete formation of the dianion of the starting material. The final deep orange solution was then stirred at 0° for 15 min before adding iodopropane (7.92 g). After 15 min, the reaction mixture was cautiously diluted with water (250 ml) and was extracted with ethyl ether (300 ml). The organic layer was washed with brine, dried (MgSO4), and evaporated to afford the title compound as a white solid, 11.38 g (97% yield). Recrystallization from hexane provided an analytical sample, m.p. 88°-89°.
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