Reaktion #346068

Reaktionsgleichung

5-(4-chlorophenyl)furan

HCl

AlCl3

3-carbomethoxypropionyl chloride

→

Methyl 4-[5-(4-Chlorophenyl)-2-furanyl]-4-oxobutanoate

Lösungsmittel

1,2-dichloroethane

1,2-dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe temperature below 25°
2. 2
   TemperaturThe reaction mixture was cooled to 15°
3. 3
   Sonstigerising to 30°
4. 4
   SonstigeThe organic layer was separated
5. 5
   Extraktionthe aqueous layer extracted with dichloromethane
6. 6
   WaschenThe combined organic layers were washed with 1000 ml of 6% sodium carbonate solution with 1000 ml of water
7. 7
   Trocknendried over MgSO4
8. 8
   SonstigeThe solvent was removed on a Calab evaporator
9. 9
   Sonstigeyielding a residual oil which
10. 10
    Extraktionwas extracted several times with refluxing hexane
11. 11
    TemperaturThe hexane extracts were cooled
12. 12
    Sonstigeto yield a solid which
13. 13
    Filtrationwas filtered
14. 14
    Waschenwashed twice with 6% sodium carbonate solution
15. 15
    Sonstigerecrystallized from hexane and air
16. 16
    Sonstigedried
17. 17
    Sonstigeto yield 7 g (5%)
18. 18
    SonstigeAn analytical sample was prepared
19. 19
    Sonstigeby drying a sample in a vacuum pistol at room temperature

Vorschrift

To a stirring mixture of 62 g (0.50 mole) of AlCl3 in 375 ml of 1,2-dichloroethane was added portionwise 75 g (0.5 mole) of 3-carbomethoxypropionyl chloride while keeping the temperature below 25° by means of an ice bath. The reaction mixture was cooled to 15° and a solution of 89 g (0.5 mole) of 5-(4-chlorophenyl)furan in 250 ml of 1,2-dichloroethane was added dropwise with HCl gas being evolved and the temperature rising to 30°. The reaction mixture was stirred at ambient temperature for 1 hour and then added to 1000 ml of ice/water. The organic layer was separated and the aqueous layer extracted with dichloromethane. The combined organic layers were washed with 1000 ml of 6% sodium carbonate solution with 1000 ml of water and dried over MgSO4. The solvent was removed on a Calab evaporator yielding a residual oil which was extracted several times with refluxing hexane. The hexane extracts were cooled to yield a solid which was filtered, washed twice with 6% sodium carbonate solution, recrystallized from hexane and air dried to yield 7 g (5%). An analytical sample was prepared by drying a sample in a vacuum pistol at room temperature, m.p. 99°-100°.

Quelle