反应详情

To a solution of potassium tert-butoxide (6.5 g, 0.058 mol) in 1,2-dimethoxyethane (150 mL) was added p-toluenesulfonylmethyl isocyanide (5.6 g, 0.029 mol) portionwise at −78° C. Then a solution of 4-bromo-2-methoxybenzaldehyde (6.3 g, 0.029 mol) in 1,2-dimethoxyethane was added dropwise and the reaction mixture was warmed to room temperature. The mixture was stirred at room temperature for 1 hour and methanol (150 mL) was added, then heated to reflux and stirred for 2 hours. Solvent was evaporated, and saturated ammonium chloride (100 mL) was added and extracted with ethyl acetate (100 mL×2). The organic layers were combined, dried over sodium sulfate and concentrated in vacuo to give a residue, which was purified by combiflash (Petroleum ether/EtOAc=10:1 to 5:1) to give the title compound (5.4 g, 82%) as a light yellow solid.

1. temperatureheated
2. temperatureto reflux
3. stirringstirred for 2 hours
4. customSolvent was evaporated
5. additionsaturated ammonium chloride (100 mL) was added
6. extractionextracted with ethyl acetate (100 mL×2)
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated in vacuo
9. customto give a residue, which
10. customwas purified by combiflash (Petroleum ether/EtOAc=10:1 to 5:1)