反应详情

温度

0 °C

To a solution of (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)pent-4-en-2-ylcarbamate (20 g, 55.0 mmol) and MeI (6.22 mL, 99.7 mmol) in DMF (700 mL) was added sodium hydride (60%, 3.1 g, 77.6 mmol) at 0° C. The reaction was stirred at 0° C. for 2 h then warmed to 10° C. for an additional 2 h at which point LC-MS analysis showed the reaction was complete. The reaction was quenched with saturated aq. NH4Cl solution (800 mL) and EtOAc (2 L). Water was then added to dissolve the solids. The organic layer was washed with water, brine, and dried over Na2SO4. The resulting residue was purified on silica gel column using a mixture of hexanes and EtOAc to give (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)pent-4-en-2-yl(methyl)carbamate (16.9 g, 81%). LRMS (M+H+) m/z 230.2.

1. temperaturethen warmed to 10° C. for an additional 2 h at which point LC-MS analysis
2. customThe reaction was quenched with saturated aq. NH4Cl solution (800 mL) and EtOAc (2 L)
3. additionWater was then added
4. dissolutionto dissolve the solids
5. washThe organic layer was washed with water, brine
6. dry with materialdried over Na2SO4
7. customThe resulting residue was purified on silica gel column
8. additiona mixture of hexanes and EtOAc