反应详情

温度

-78 °C

To a chilled solution (−78° C.) of 9.33 g (47.55 mmol) of 2-(3-fluorophenoxy)-tetrahydro-2H-pyran in 150 mL of THF was added 38 mL (95.1 mmols) of n-BuLi (2.5 M soln in hexanes). The reaction mixture was stirred at −78° C. for 45 minutes and slowly added 11.9 mL (190.2 mmol) of methyl iodide via syringe. The reaction was allowed to warm to room temperature and was stirred overnight. Quenched reaction with satd ammonium chloride and transferred to a round bottom flask. Removed volatiles in vacuo and partitioned mixture between EtOAc and water. Separated layers and washed organics with water (×2) and brine. Dried over Na2SO4, filtered, and concd to afford a 9.01 g (90%) of a yellow oil: 1H NMR (CDCl3/400 MHz) 1.46-2.09 (m, 6H), 2.21 (d, 3H, J=2.0 Hz), 3.60-3.65 (m, 1H), 3.86-3.92 (m, 1H), 5.44 (t, 1H, J=3.2 Hz), 6.70 (t, 1H, J=8.8 Hz), 6.90 (d, 1H, J=8.4 Hz), 7.08 (dd, 1H, J=8.0, 15.2 Hz); HRMS (EI+) m/z calcd for (C12H15FO2) 210.1056, found 210.1070.

1. temperatureto warm to room temperature
2. stirringwas stirred overnight
3. customQuenched
4. customreaction with satd ammonium chloride
5. customtransferred to a round bottom flask
6. customRemoved volatiles in vacuo and partitioned mixture between EtOAc and water
7. washSeparated layers and washed organics with water (×2) and brine
8. dry with materialDried over Na2SO4
9. filtrationfiltered