Réaction #531796

Équation de réaction

compound 25

N-(11-(p-tolyloxy)undecyl)-3-(tritylthio)propaneamide

trifluoroacetic acid

triethylsilane

→

N-(11-(p-tolyloxy)undecyl)-3-mercaptopropaneamide

Solvants

methylene chloride

methylene chloride

Conditions de réaction

Traitement

1. 1
   Autreto obtain a brown-colored solution
2. 2
   workup.DISTILLATIONthe supernatant solution was distilled away under reduced pressure
3. 3
   AutreThe solid obtained
4. 4
   Lavagewas washed twice with 30 ml of aqueous saturated sodium hydrogen carbonate solution and twice with 30 ml of saturated brine
5. 5
   Autrethe desiccant agent was removed by filtration
6. 6
   workup.DISTILLATIONthe solvent of the filtrate was distilled away under reduced pressure
7. 7
   AutreThe reaction mixture was purified by chromatography, and 0.1 g of the compound f, which
8. 8
   Autrewas obtained

Mode opératoire

The compound 25 (0.181 g) was dissolved in 1 ml of methylene chloride, and 0.5 ml of trifluoroacetic acid was added to that while being stirred, to obtain a brown-colored solution. After a white-colored precipitate was generated by adding 0.16 ml of triethylsilane, the supernatant solution was distilled away under reduced pressure. The solid obtained was dissolved by the new addition of 20 ml of methylene chloride, and was washed twice with 30 ml of aqueous saturated sodium hydrogen carbonate solution and twice with 30 ml of saturated brine. After the collected organic phase 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 0.1 g of the compound f, which was a white solid, was obtained.

Source