반응 #6304

반응 방정식

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

용매

dimethylformamide

dimethylformamide

HCl

water

반응 조건

후처리

1. 1
   온도heating
2. 2
   온도After cooling to room temperature
3. 3
   추출the mixture is extracted with three portions of ether
4. 4
   건조The combined organics are dried over 4A sieves
5. 5
   여과filtered through cotton
6. 6
   기타evaporated
7. 7
   기타The crude reaction product
8. 8
   추출After careful neutralization with saturated sodium bicarbonate, the aqueous mixture is extracted with three portions of ether
9. 9
   건조dried over 4A sieves
10. 10
    여과filtered through cotton
11. 11
    기타evaporated

실험 절차

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.

출처