Dissolve 2-adamantanone (1.50 g, 10 mmol) in ether under nitrogen protection and cool to 0°C. Methyl lithium solution (7.5 mL, 1.6 M in ether, 12 mmol) was added slowly and dropwise. The reaction mixture was continued to be stirred at 0 °C for 1 h, then brought to room temperature and stirred overnight. Upon completion of the reaction, the reaction was quenched by the addition of saturated ammonium chloride solution and extracted three times with ether. The organic phases were combined, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product was purified by fast column chromatography (eluent: dichloromethane to 5% methanol/dichloromethane) to afford 2-methyl-2-adamantanol (56) as a white solid (1.58 g, 95% yield).1H-NMR (360 MHz, CDCl3) δ 2.20-2.16 (m, 2H), 1.89-1.75 (m, 6H), 1.68 ( br s, 4H), 1.57-1.54 (m, 2H), 1.48 (br s, 1H), 1.35 (s, 3H); 13C-NMR (90 MHz, CDCl3) δ 74.06, 39.30, 38.49, 35.33, 33.16, 27.73, 27.60, 27.22; ESI-MS: C11H18O(M+H)+ calculated value 167.3, measured value 167.3.
