Reaktion #82460

Reaktionsgleichung

ethylmalonamate

diethyl ethoxymethyleneoxalacetate

sodium acetate

→

title product

Ausbeute 80.3%

triethyl-1,6-dihydro-6-oxo-2,3,5-pyridinetricarboxylate

Ausbeute 80.3%

Lösungsmittel

ethanol

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture is heated
2. 2
   Temperaturto reflux
3. 3
   workup.STIRRINGstirred for 13.5 hours
4. 4
   TemperaturAfter cooling
5. 5
   Sonstigethe ethanol is removed under vacuum
6. 6
   workup.ADDITIONthe residue diluted with water
7. 7
   ExtraktionThe aqueous solution is extracted with methylene chloride (2×200 mL)
8. 8
   Waschenthe organic layer washed with 300 mL saturated sodium chloride
9. 9
   Trocknendried over anhydrous magnesium sulfate
10. 10
    Einengenconcentrated in vacuum

Vorschrift

A solution of ethylmalonamate (23.6 g, 0.18 mol) in absolute ethanol (300 mL) is added to a stirred solution of diethyl ethoxymethyleneoxalacetate (44.0 g, 0.18 mol) in ethanol (200 mL) at 0° C., followed by the addition, of solid sodium acetate (14.72 g, 0.18 mol). After stirring for ten minutes at 0° C., the mixture is heated to reflux and stirred for 13.5 hours. After cooling, the ethanol is removed under vacuum, and the residue diluted with water and acidified to pH 2 with concentrated hydrochloric acid. The aqueous solution is extracted with methylene chloride (2×200 mL) and the organic layer washed with 300 mL saturated sodium chloride, then dried over anhydrous magnesium sulfate and concentrated in vacuum to give 45.0 g of the title product as an orange oil.

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