C(NC(C)C)(C)C.C([Li])CCC.[N:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]2)=[CH:15][CH:14]=1.[C:26](C1NC=CN=1)(=[O:28])[CH3:27]>O1CCCC1.CCCCCC>[C:26]([CH:21]1[CH2:20][CH:19]([C:16]2[CH:17]=[CH:18][N:13]=[CH:14][CH:15]=2)[CH2:24][CH2:23][C:22]1=[O:25])(=[O:28])[CH3:27]
To a solution of 3.2 ml of diisopropylamine dissolved in 40 ml of tetrahydrofuran, there was added 14.2 ml of 1.6M solution of n-butyl lithium in hexane at -20° C. Then, a solution of 2 g of 4-(4-pyridyl)cyclohexanone dissolved in 40 ml of tetrahydrofuran was added at -40° C. The reaction mixture was cooled to -78° C., and 2.5 g of acetylimidazole dissolved in 40 ml of tetrahydrofuran was added. The reaction mixture was stirred at room temperature, poured into ice water, and then washed with ether. The aqueous layer was saturated with ammonium chloride and extracted with methylene chloride. Thus, there was obtained 1.65 g of 2-acetyl-4-(4-pyridyl)cyclohexanone.
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