反応 #531793

反応方程式

compound 14

3-(tritylthio)propionic acid

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

compound 16

11-(p-tolyloxy)undecan-1-ol

→

11-(p-tolyloxy)undecyl 3-(tritylthio)propioate

溶媒

methylene chloride

反応条件

後処理

1. 1
   その他the reaction solution was moved into a separating funnel
2. 2
   洗浄was washed twice with 100 ml of 10% aqueous potassium hydrogen sulfate solution, twice with 100 ml of aqueous saturated sodium hydrogen carbonate solution, twice with 100 ml of ion-exchange water
3. 3
   その他After the methylene chloride phase collected
4. 4
   その他the desiccant agent was removed by filtration
5. 5
   workup.DISTILLATIONthe solvent of the filtrate was distilled away under reduced pressure
6. 6
   その他The reaction mixture was purified by chromatography, and 2.63 g of 11-(p-tolyloxy)undecyl 3-(tritylthio)propioate 17, which
7. 7
   その他was obtained

実験手順

The compound 14 (1.86 g), 0.896 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC), and 0.029 g of 4-dimethylaminopyridine (DMAP) were dissolved in 300 ml of methylene chloride. After the compound 16 (3.04 g) was then added and stirred at room temperature for 24 hours, the reaction solution was moved into a separating funnel, and was washed twice with 100 ml of 10% aqueous potassium hydrogen sulfate solution, twice with 100 ml of aqueous saturated sodium hydrogen carbonate solution, twice with 100 ml of ion-exchange water, and twice with 100 ml of saturated brine. After the methylene chloride phase collected was dehydrated with magnesium sulfate, the desiccant agent was removed by filtration, and the solvent of the filtrate was distilled away under reduced pressure. The reaction mixture was purified by chromatography, and 2.63 g of 11-(p-tolyloxy)undecyl 3-(tritylthio)propioate 17, which was a white solid, was obtained.

出典