反应详情

温度

80 °C

In an argon-charged flask, 2M sodium carbonate (4.8 mmol), 1,2-dimethoxyethane (8 ml), 4-fluorophenylboric acid (2.8 mmol), lithium chloride (6 mmol), 1,4-dioxaspiro[4.5]dec-7-en-8-yl-trifluormethane-sulphonic acid ester (2 mmol) and tetrakis(triphenyl-phosphine)palladium (0.1 mmol) are combined and stirred overnight at 80° C. The reaction mixture is concentrated in a vacuum and the residue is dispersed in dichloromethane/2M aqueous sodium carbonate solution. The aqueous phase is extracted with dichloromethane. The combined organic phases are then dried over sodium sulphate and the solvent is evaporated off in a vacuum. From the residue, after column chromatography using silica gel (ethyl acetate/heptane 1:4), pure 8-(4-fluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene is isolated (Synthesis 1993, 735-762): tR 3.61 min (LC-1); ESI-MS(+): m/z 235.34 [M+H]+. 1H NMR (ppm,CDCl3): 7.35 (2H); 6.95 (2H); 5.9 (1H); 4.05 (4H); 2.65 (2H); 2.45 (2H); 1.9 (2H).

1. additionIn an argon-charged flask
2. concentrationThe reaction mixture is concentrated in a vacuum
3. additionthe residue is dispersed in dichloromethane/2M aqueous sodium carbonate solution
4. extractionThe aqueous phase is extracted with dichloromethane
5. dry with materialThe combined organic phases are then dried over sodium sulphate
6. customthe solvent is evaporated off in a vacuum