反应详情

温度

-78 °C

Phosphonate 4 (3.2 g, 10 mmol) was dissolved in 30 ml dry THF under argon and cooled to -78° C. Dropwise addition of nBuLi (2.3M, 4.4 ml, 10.1 mmol) generated a yellow-orange phosphonate ylid. After stirring the ylid solution for 10 min, 5-chloro-2 adamantanone (1.75 g, 9.5 mmol), dissolved in 8 ml THF, was added dropwise to the ylid at -78° C. The reaction was slowly warmed to room temperature over 45 min and refluxed for 2 h. Upon cooling, the THF was stripped in vacuo and the product was partitioned between EtOAc/hexanes (1:1) and dilute NaHCO3. The organic layer was dried over NaHCO3. The organic layer was dried over Na2SO4, stripped of solvent and purified on silica gel (2-4% EtOAc/hexanes) to give 3.3 g (96%) of enol ether 5 as a colorless, viscous gum.

1. additionwas added dropwise to the ylid at -78° C
2. temperatureThe reaction was slowly warmed to room temperature over 45 min
3. temperaturerefluxed for 2 h
4. temperatureUpon cooling
5. customthe product was partitioned between EtOAc/hexanes (1:1) and dilute NaHCO3
6. dry with materialThe organic layer was dried over NaHCO3
7. dry with materialThe organic layer was dried over Na2SO4
8. custompurified on silica gel (2-4% EtOAc/hexanes)