Reacción #6304

Ecuación de reacción

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

Disolventes

dimethylformamide

dimethylformamide

HCl

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheating
2. 2
   TemperaturaAfter cooling to room temperature
3. 3
   Extracciónthe mixture is extracted with three portions of ether
4. 4
   SecadoThe combined organics are dried over 4A sieves
5. 5
   Filtraciónfiltered through cotton
6. 6
   Otroevaporated
7. 7
   OtroThe crude reaction product
8. 8
   ExtracciónAfter careful neutralization with saturated sodium bicarbonate, the aqueous mixture is extracted with three portions of ether
9. 9
   Secadodried over 4A sieves
10. 10
    Filtraciónfiltered through cotton
11. 11
    Otroevaporated

Procedimiento

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.

Fuente