2,4-己二烯酸,6-溴-,甲酯,(E,E)-

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 6-bromo-hexa-2,4-dienoic acid methyl ester (1.57 g, 7.66 mmol) and 2-thionaphthol (1.35 g, 8.42 mmol) in diethyl ether (40 mL) was added dropwise triethylamine (1.40 mL, 10.0 mmol) under an atmosphere of argon. The mixture was stirred for one hour 20° C. and filtered. The filtrate was washed saturated aqueous sodium hydrogen carbonate (25 mL), demineralised water (25 mL) and brine (25 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 8:2 40-60° C. petroleum ether:diethyl ether). Recrystallisation from diethyl ether/petroleum ether afforded the title compound (1.9 g, 88%) as a white solid, mp 73-75° C. filtered The filtrate was washed saturated aqueous sodium hydrogen carbonate (25 mL), demineralised water (25 mL) and brine (25 mL) The organic layer was dried over anhydrous MgSO4 filtered concentrated under reduced pressure to give a yellow oil that was purified by column chromatography (9:1 to 8:2 40-60° C. petroleum ether:diethyl ether) Recrystallisation from diethyl ether/petroleum ether

反应条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 6-bromohexa-2,4-dienoic acid methyl ester (0.41 g, 2.0 mmol), sodium benzene sulfinate (0.33 g, 2.0 mmol) and tetra-n-butylammonium iodide (37 mg, 0.1 mmol) was heated at reflux in dry THF (10 mL) under an atmosphere of nitrogen for 2 hours. The resulting slurry was allowed to cool to 20° C. and filtered. The filtrate was concentrated under reduced pressure to give an oil that was dissolved in ethyl acetate (20 mL). This solution was washed successively with saturated aqueous sodium hydrogen carbonate (10 mL), distilled water (10 mL), then with brine (10 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give an oil that was purified by flash chromatography (7:3 to 1:1 to 1:1 60-80° C. petroleum ether:diethyl ether) to give a solid that was recrystallised to give the title compound (0.39 g, 73%) as white crystals, mp 105° C. was heated filtered The filtrate was concentrated under reduced pressure to give an oil that This solution was washed successively with saturated aqueous sodium hydrogen carbonate (10 mL) distilled water (10 mL) The organic layer was dried over anhydrous MgSO4 filtered concentrated under reduced pressure to give an oil that was purified by flash chromatography (7:3 to 1:1 to 1:1 60-80° C. petroleum ether:diethyl ether) to give a solid that was recrystallised