Cyclohexanone → 1-(2-((Tert-butyldimethylsilyloxy)methyl)-4-(trifluoromethyl)phenyl)cyclohexanol

Participants

Reaction Conditions

Reaction Steps

To a solution of (2-bromo-5-(trifluoromethyl)benzyloxy)(tert-butyl)dimethylsilane (140 mg; 0.379 mmol) in tetrahydrofuran (0.5 mL) at −78° C. was added dropwise n-butyllithium (0.4 mL; 0.64 mmol; 1.6M in hexanes). The reaction was stirred at −78° C. for 15 minutes. Cyclohexanone (0.8 mL; 7.7 mmol) was added stirred at −78° C. for 10 minutes. The reaction was then stirred at room temperature for 15 minutes. The reaction was quenched with 2 drops of water. It was diluted with ethyl acetate and filtered through a column containing silica gel and sodium sulfate. The crude was then purified over a 12 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 10-40% ethyl acetate in heptane) to give 112 mg (76%) as a liquid. MS (ES+): Calc: 388.5, Found: 433.2 (M+HCO2−) 1H NMR (400 MHz, CDCl3) δ ppm 7.58 (s, 1H), 7.51 (d, J=8.30 Hz, 1H), 7.45 (d, J=8.30 Hz, 1H), 5.05 (s, 2H), 3.92 (s, 1H), 1.94-1.73 (m, 6H), 1.68-1.6 (m, 2H), 1.31 (m, 2H), 0.93 (s, 9H), 0.12 (s, 6H).

Provenance & Evidence