反应详情

温度

0 °C

To a solution of (2-bromo-5-(trifluoromethyl)benzyloxy)(tert-butyl)dimethylsilane (1.3 g, 3.5 mmol) in THF at 0° C. was added i-PrMgCl/LiCl in THF (3.5 mL, 4.5 mmol). The mixture was stirred at 0° C. for 4 hours and cyclohexanecarboxaldehyde (0.61 g, 0.65 mL, 5.4 mmol) was added. The mixture was stirred at 0° C.-room temperature for 1 hour, quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate. Combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography over 25+M Biotage silica column (eluted with 0-20% ethyl acetate in heptane) to afford the title compound (1.27 g, 90%). 1H NMR (400 MHz, CDCl13) δ ppm 0.13 (s, 6H) 0.94 (s, 9H) 0.96-1.38 (m, 7H) 1.63-1.73 (m, 2H) 1.77-1.83 (m, 1H) 2.06(d, J=13.28 Hz, 1H) 2.28 (d, J=3.73 Hz, 1H) 4.58 (dd, J=7.68, 3.94 Hz, 1H) 4.75 (d, J=13.28 Hz, 1H) 4.85 (d, J=13.28 Hz, 1H) 7.53 (s, 2H) 7.68 (s, 1H).

1. stirringThe mixture was stirred at 0° C.-room temperature for 1 hour
2. customquenched with saturated aqueous ammonium chloride
3. extractionextracted with ethyl acetate
4. washCombined organic layers were washed with brine
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated in vacuo
7. customThe residue was purified by chromatography over 25+M Biotage silica column (eluted with 0-20% ethyl acetate in heptane)