反应详情

To a suspension prepared by suspending 1.52 g (38.0 mmol) of 60% sodium hydride in 15 ml of THF was added dropwise solution of 5.29 g (17.3 mmol) of the 4-(trans-4-n-pentylcyclohexyl)-phenyldithiocarboxylic acid obtained by the first step, in 20 ml of THF under a condition cooled with ice in 15 min, and stirred as it was for 30 min. To this reaction solution was added dropwise solution of 2.50 g (14.4 mmol) of 2,3-difluoro-4-ethoxyphenol in 20 ml of THF in 15 min and stirred as it was for 30 min. To this reaction solution was added dropwise solution of 9.64 g (38.0 mmol) of iodine in 20 ml of THF in 15 min, stirred as it was for 1 hour, warmed up to room temperature, and then stirred at the same temperature overnight. This reaction solution was poured into 10% aqueous sodium thiosulfate solution and extracted with 100 ml of diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under a reduced pressure, and the residue was purified by silica gel column chromatography (eluent: heptane) and further recrystallized from heptane to obtain 2.0 g of 2,3-difluoro-4-ethoxyphenyl 4-(trans-4-n-pentylcyclohexyl)thiobenzoate (yield 31.2%).

1. customTo a suspension prepared
2. temperaturecooled with ice in 15 min
3. stirringstirred as it
4. waitwas for 30 min
5. stirringstirred as it
6. waitwas for 1 hour
7. stirringstirred at the same temperature overnight
8. extractionextracted with 100 ml of diethyl ether
9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
10. distillationthe solvent was distilled off under a reduced pressure
11. customthe residue was purified by silica gel column chromatography (eluent: heptane)
12. customfurther recrystallized from heptane