To a 250 mL round bottom flask equipped with stirbar was added N-(1-Phenylethylidene)cyclohexanamine (13.0 g, 0.064 mol 1 equiv) and THF (18 mL). The flask was sealed with a rubber septum, placed under a nitrogen atmosphere via a nitrogen inlet needle, and stirred via a magnetic stir plate. The reaction mixture was cooled to 0 ^oC in an ice-water bath for approximately 10 minutes. To this chilled mixture was added a 2 M solution of lithium diisopropylamide¹ in THF/ethylbenzene/heptane (35.2 mL, 0.0704 mol, 1.1 equiv) dropwise via a 60 mL syringe.² The reaction mixture was allowed to stir for 1 hour at 0 ^oC.³ After this time, (iodomethyl)trimethylsilane  (19.44 g, 0.0704 mol, 1.1 equiv) was added dropwise via a 30 mL syringe. The reaction mixture was allowed to stir for 1 hour at 0 oC. After this time, the septa was removed and 65 mL of an acetate buffer (32.5 g NaOAc•3H2O, 65 mL HOAc, 65 mL H2O) was added all at once. Initially a precipitate formed but dissolved after stirring for 10 minutes at 0 oC. The reaction mixture was transferred to a large separatory funnel and diluted with pentane⁴ (≈400 mL) and water (≈100 mL). The layers were separated and the aqueous layer was extracted three times with pentane (≈50 mL each). The organic layers were combine and were washed with a saturated sodium bicarbonate solution in a separatory funnel (CAUTION: The pentane layer contains some acetic acid. Quenching this with the bicarbonate solution releases CO2 gas and hence the separatory funnel must be vented often to avoid pressure build-up). The washes were continued until no more gas was evolved (roughly three washes of 50 mL each). The organic layer was washed with brine (≈ 200 mL) and dried with Na₂SO₄. The solvent was removed in vacuo and then purified via vacuum distillation (b.p. 140-143 ^oC @ 0.10 mmHg) giving the ketone (15.24 g, 88%) as a clear, light yellow oil.

Fleming, I.; Patel, S. K.; Urch, C. J. Chem. Soc. Perk. Trans. I 1989, 115.