Réaction #6304

Équation de réaction

sodium chloride

N-acetoxyhexyl-1,2,3,4-tetrahydroquinoline-6-carboxaldehyde

1,3-dioxolan-2-ylmethyltributylphosphonium bromide

Potassium t-butoxide

→

3-(N-hydroxyhexyl-1,2,3,4-tetrahydroquinolin-6-yl)acrolein

Solvants

dimethylformamide

dimethylformamide

HCl

water

Conditions de réaction

Traitement

1. 1
   Températureheating
2. 2
   TempératureAfter cooling to room temperature
3. 3
   Extractionthe mixture is extracted with three portions of ether
4. 4
   SéchageThe combined organics are dried over 4A sieves
5. 5
   Filtrationfiltered through cotton
6. 6
   Autreevaporated
7. 7
   AutreThe crude reaction product
8. 8
   ExtractionAfter careful neutralization with saturated sodium bicarbonate, the aqueous mixture is extracted with three portions of ether
9. 9
   Séchagedried over 4A sieves
10. 10
    Filtrationfiltered through cotton
11. 11
    Autreevaporated

Mode opératoire

To a solution 30.3 g (0.1 mole) of N-acetoxyhexyl-1,2,3,4-tetrahydroquinoline-6-carboxaldehyde in dimethylformamide is added 7.4 g (0.2 mole) of 1,3-dioxolan-2-ylmethyltributylphosphonium bromide in dimethylformamide with magnetic stirring, and the mixture is heated at 90° C. Potassium t-butoxide (22.4 g, 0.2 mole) is added, and heating is continued at 90° C. for 16 hours. After cooling to room temperature, the solution is poured into a seven-fold excess of water. The aqueous mixture is saturated with sodium chloride, and the mixture is extracted with three portions of ether. The combined organics are dried over 4A sieves, filtered through cotton, and evaporated. The crude reaction product is then dissolved in 3M HCl, and the reaction is stirred at room temperature for 16 hours. After careful neutralization with saturated sodium bicarbonate, the aqueous mixture is extracted with three portions of ether, and the combined organics are passed through silica gel, dried over 4A sieves, filtered through cotton, and evaporated to yield 3-(N-hydroxyhexyl-1,2,3,4-tetrahydroquinolin-6-yl)acrolein.

Source