Reacción #57423

Ecuación de reacción

sodium ethoxide

diethyl oxalate

acetone

sodium

sulfuric acid

sodium

→

expected product

Rendimiento 101.0%

Ethyl 2-hydroxy-4-oxopent-2-enoate

Rendimiento 101.0%

Disolventes

water

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrois prepared
2. 2
   Otroat ambient temperature
3. 3
   Otrohas been completely consumed
4. 4
   TemperaturaThe reaction medium is maintained
5. 5
   ConcentraciónThe reaction medium is subsequently concentrated under vacuum
6. 6
   OtroThe crude reaction product
7. 7
   Otrois obtained
8. 8
   ExtracciónThe resulting aqueous phase is extracted with ethyl acetate (3×300 mL)
9. 9
   Secadodried over MgSO4
10. 10
    Concentraciónconcentrated under vacuum
11. 11
    OtroThe crude reaction product
12. 12
    Otrois dried under vacuum
13. 13
    Otroto give

Procedimiento

In a 2-liter three-neck round-bottom flask equipped with a dropping funnel and a paddle stirrer a solution of sodium ethoxide is prepared by reacting metallic sodium (7.74 g, 340.00 mmol, 1.2 eq) in anhydrous ethanol (800 ml) at ambient temperature until the metallic sodium has been completely consumed. A solution of diethyl oxalate (37.20 mL, 280.00 mmol, 1.0 eq) in acetone (10.30 mL, 280.00 mmol, 1.0 eq) is subsequently added dropwise at ambient temperature. The reaction medium is maintained with vigorous stirring for 2 hours. The reaction medium is subsequently concentrated under vacuum. The crude reaction product is diluted in water (200 ml). Ice (100 g) is added, followed by concentrated sulfuric acid (20 ml) in small portions, until a clear orange solution is obtained. The resulting aqueous phase is extracted with ethyl acetate (3×300 mL). The organic phases are combined, dried over MgSO4 and then concentrated under vacuum. The crude reaction product is dried under vacuum to give, quantitatively, the expected product (m=44.71 g).

Fuente