Source:
n-Butyllithium  (14.0 mL of a 2.5 M solution in hexane, 35 mmol) was added dropwise to a solution of 2,6-dimethylanisole  (4.95 mL, 35 mmol) in 60 mL of tetrahydrofuran  at 0°, and the resulting solution was stirred at 0° for 1 hour and then at ambient temperature for 4 hours. The reaction mixture was cooled to 0°, treated with cyclohexanecarboxaldehyde  (4.2 mL, 35 mmol), allowed to warm to ambient temperature again, and poured into saturated aqueous ammonium chloride solution. The mixture was extracted with ether and the ether extract was washed with water and brine and concentrated in vacuo. The residue was purified by silica gel chromatography (hexane-ether, 5:1 v/v) to give 4.2 g (48%) of the product as a colorless oil; H NMR (CDCl) δ 1.05–1.50 (m, 6H), 1.64–1.82 (m, 4H), 1.92 (m, 1H), 2.28 (d, 1H, J = 3 Hz), 2.31 (s, 3H), 2.68 (dd, 1H, J = 10, 13 Hz), 2.85 (dd, 1H, J = 3, 13 Hz), 3.57 (m, 1H), 3.75 (s, 3H), 6.95–7.10 (m, 3H).