Réaction #57423

Équation de réaction

sodium ethoxide

diethyl oxalate

acetone

sodium

sulfuric acid

sodium

→

expected product

Rendement 101.0%

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

Rendement 101.0%

Solvants

water

ethanol

Conditions de réaction

Traitement

1. 1
   Autreis prepared
2. 2
   Autreat ambient temperature
3. 3
   Autrehas been completely consumed
4. 4
   TempératureThe reaction medium is maintained
5. 5
   ConcentrationThe reaction medium is subsequently concentrated under vacuum
6. 6
   AutreThe crude reaction product
7. 7
   Autreis obtained
8. 8
   ExtractionThe resulting aqueous phase is extracted with ethyl acetate (3×300 mL)
9. 9
   Séchagedried over MgSO4
10. 10
    Concentrationconcentrated under vacuum
11. 11
    AutreThe crude reaction product
12. 12
    Autreis dried under vacuum
13. 13
    Autreto give

Mode opératoire

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).

Source