反応 #516892

反応方程式

sodium hydride

2,3-difluoro-4-ethoxyphenol

sodium thiosulfate

iodine

4-(trans-4-n-pentylcyclohexyl)-phenyldithiocarboxylic acid

→

2,3-difluoro-4-ethoxyphenyl 4-(trans-4-n-pentylcyclohexyl)thiobenzoate

収率 31.2%

溶媒

THF

THF

THF

THF

反応条件

後処理

1. 1
   その他To a suspension prepared
2. 2
   温度cooled with ice in 15 min
3. 3
   workup.STIRRINGstirred as it
4. 4
   workup.WAITwas for 30 min
5. 5
   workup.STIRRINGstirred as it
6. 6
   workup.WAITwas for 1 hour
7. 7
   workup.STIRRINGstirred at the same temperature overnight
8. 8
   抽出extracted with 100 ml of diethyl ether
9. 9
   乾燥The organic layer was dried over anhydrous magnesium sulfate
10. 10
    workup.DISTILLATIONthe solvent was distilled off under a reduced pressure
11. 11
    その他the residue was purified by silica gel column chromatography (eluent: heptane)
12. 12
    その他further recrystallized from heptane

実験手順

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%).

出典