Diethyl 2-(ethoxymethylidene)-3-oxobutanedioate → Triethyl 1,6-dihydro-6-oxo-2,3,5-pyridinetricarboxylate

HRID 742209

Reaktionsgleichung

C([CH:3]([C:7]([NH2:9])=[O:8])[C:4]([O-:6])=[O:5])C.C(O[CH:13]=[C:14]([C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16])C.[C:27]([O-])(=O)[CH3:28].[Na+]>C(O)C>[CH2:25]([O:24][C:22]([C:20]1[NH:9][C:7](=[O:8])[C:3]([C:4]([O:6][CH2:27][CH3:28])=[O:5])=[CH:13][C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:23])[CH3:26]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

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 co 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.

Aufarbeitung

temperaturethe mixture is heated
temperatureto reflux
stirringstirred for 13.5 hours
temperatureAfter cooling
customthe ethanol is removed under vacuum
additionthe residue diluted with water
extractionThe aqueous solution is extracted with methylene chloride (2×200 mL)
washthe organic layer washed with 300 mL saturated sodium chloride
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuum

Quellen und Nachweise

ORD-Eintrag: ord-efbaab2ebdd047b2a926ccdcd794ff5e
Quelldatensatz: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05554579

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