反应详情

To a slurry of 60% NaH (125 mg, 3.12 mmol) in DME (3571 mL) at 0° C. was added 2-phenylcyclopentanone (500 mg, 3.12 mmol). After stirring for 1 h, MeI (898 μL, 14.36 mmol) was added, and the solution heated to reflux for 2 h. The reaction was poured onto ice and extracted 3 times into Et2O. The organic extracts were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. Applied to Silica gel and eluted with an EtOAc/Hex gradient to afford 2-methyl-2-phenylcyclopentanone (401.7 mg, 2.305 mmol, 73.9% yield). LC-MS (M+H)+=175.1. 1H NMR (500 MHz, CDCl3) δ ppm 7.29-7.37 (4 H, m), 7.20-7.24 (1 H, m), 2.54 (1 H, dt, J=12.51, 6.26 Hz), 2.34 (2H, t, J=7.63 Hz), 1.82-2.05 (3 H, m), 1.38 (3 H, s).

1. temperaturethe solution heated
2. temperatureto reflux for 2 h
3. additionThe reaction was poured onto ice
4. extractionextracted 3 times into Et2O
5. washThe organic extracts were washed with brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. washApplied to Silica gel and eluted with an EtOAc/Hex gradient