反应详情

温度

0 °C

To a suspension of 3.92 g (97.5 mmol, 3 equiv) of 60% NaH in mineral oil (washed three times with pentane) in 200 mL of tetrahydrofuran at 0° C. under argon was added dropwise a solution of 15.3 mL (107 mmol, 3.3 equiv) of ethyl propionylacetate. After 0.5 hour, a solution of 7.04 g (32.4 mmol) of (E)-geranyl bromide in 20 mL of tetrahydrofuran was added dropwise over 45 minutes. The mixture was stirred one hour at 0° C. and one hour at room temperture, quenched with NH4Cl and diluted with 500 mL of diethyl ether. The organic layer was washed with water and brine, and dried over MgSO4 to obtain 20.157 g of crude product as a yellow oil. Purification by flash chromatography on 800 g of silica gel, eluted with 3:97 ethyl acetate:hexanes provided 7.024 g (77%) of pure product as a clear, colorless oil.

1. washin mineral oil (washed three times with pentane) in 200 mL of tetrahydrofuran at 0° C. under argon
2. customquenched with NH4Cl
3. additiondiluted with 500 mL of diethyl ether
4. washThe organic layer was washed with water and brine
5. dry with materialdried over MgSO4
6. customto obtain 20.157 g of crude product as a yellow oil
7. customPurification by flash chromatography on 800 g of silica gel
8. washeluted with 3:97 ethyl acetate