反应 #531793

反应方程式

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

溶剂

methylene chloride

反应条件

后处理

1. 1
   其他the reaction solution was moved into a separating funnel
2. 2
   洗涤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
   其他After the methylene chloride phase collected
4. 4
   其他the desiccant agent was removed by filtration
5. 5
   workup.DISTILLATIONthe solvent of the filtrate was distilled away under reduced pressure
6. 6
   其他The reaction mixture was purified by chromatography, and 2.63 g of 11-(p-tolyloxy)undecyl 3-(tritylthio)propioate 17, which
7. 7
   其他was obtained

实验过程

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.

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