반응 #2459097

반응 방정식

1-chloro-cyclopropyl chloromethyl ketone

ethyl bromide

magnesium

2-thienylethine

ammonium chloride

→

1-chloro-2-(1-chloro-cyclopropyl)-4-(thiophen-2-yl)-but-3-in-2-ol

수율 97.3%

용매

diethyl ether

diethyl ether

반응 조건

후처리

1. 1
   workup.ADDITIONAfter completion of the addition
2. 2
   온도the reaction mixture is heated
3. 3
   온도under reflux for 30 minutes
4. 4
   온도The mixture is heated
5. 5
   온도under reflux for 1 hour
6. 6
   온도again cooled to room temperature
7. 7
   workup.STIRRINGwith stirring
8. 8
   온도the mixture is then heated
9. 9
   온도under reflux for a further 2 hours
10. 10
    온도After cooling to room temperature
11. 11
    추출the mixture is extracted three times with diethyl ether
12. 12
    세척The combined organic phases are washed once with water
13. 13
    건조dried over sodium sulphate
14. 14
    농축concentrated under reduced pressure

실험 절차

22.2 g (0.203 mole) of ethyl bromide are slowly added to 4.9 g (0.203 mole) of magnesium turnings in 100 ml of diethyl ether. After completion of the addition, the reaction mixture is heated under reflux for 30 minutes and then cooled to room temperature, and a solution of 20 g (0.185 mole) of 2-thienylethine in 50 ml of diethyl ether is subsequently added dropwise with stirring. The mixture is heated under reflux for 1 hour and again cooled to room temperature. 28.3 g (0.185 mole) of 1-chloro-cyclopropyl chloromethyl ketone are added dropwise with stirring and the mixture is then heated under reflux for a further 2 hours. After cooling to room temperature, the reaction mixture is poured into a saturated aqueous ammonium chloride solution and the mixture is extracted three times with diethyl ether. The combined organic phases are washed once with water, dried over sodium sulphate and concentrated under reduced pressure. 47.0 g (97% of theory) of 1-chloro-2-(1-chloro-cyclopropyl)-4-(thiophen-2-yl)-but-3-in-2-ol are obtained in this way in the form of an oil which is reacted further without additional purification.

출처