反应详情

温度

20 °C

To a solution of 6-bromo-hexa-2,4-dienoic acid methyl ester (1.15 g, 5.6 mmol) and 4-dimethylamino-benzenethiol (0.86 g, 5.6 mmol) in tetrahydrofuran (30 mL) was added dropwise triethylamine (1.6 mL, 11.4 mmol) under an atmosphere of argon. The mixture was stirred at 20° C. for 30 minutes, then filtered. The filtrate was concentrated under reduced to pressure and the residue was dissolved in ethyl acetate (100 mL). This solution was washed with saturated aqueous sodium hydrogen carbonate (50 mL), demineralised water (50 mL) and brine (50 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give a yellow oil that was purified by column chromatography (9:1 to 7:3 60-80° C. petroleum ether:diethyl ether, all eluant containing 1% triethylamine by volume). The solid was recrystallised from diethyl ether/petroleum ether to give the title compound (1.0 g, 64%) as a white solid, mp 68-70° C.

1. filtrationfiltered
2. concentrationThe filtrate was concentrated
3. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
4. washThis solution was washed with saturated aqueous sodium hydrogen carbonate (50 mL), demineralised water (50 mL) and brine (50 mL)
5. dry with materialThe organic layer was dried over anhydrous MgSO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customto give a yellow oil that
9. customwas purified by column chromatography (9:1 to 7:3 60-80° C. petroleum ether
10. additiondiethyl ether, all eluant containing 1% triethylamine by volume)
11. customThe solid was recrystallised from diethyl ether/petroleum ether