Réaction #531793

Équation de réaction

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

Solvants

methylene chloride

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source