Dimethyl malonate → 5,5-bis(methoxycarbonyl)-3-methoxy-2E-pentenoic acid methyl ester

HRID 1196170

Reaktionsgleichung

Reaktionsgleichung von HRID 1196170
[CH3:1][O:2][C:3](=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].C[O-].[Na+].[CH3:13][O:14][C:15](=[O:22])/[CH:16]=[C:17](/[O:20][CH3:21])\[CH2:18]Cl>CN(C=O)C>[CH3:13][O:14][C:15](=[O:22])/[CH:16]=[C:17](/[O:20][CH3:21])\[CH2:18][CH:4]([C:5]([O:7][CH3:8])=[O:6])[C:3]([O:2][CH3:1])=[O:9]

Komponenten

5

Edukt 3

HCID 7943Dimethyl malonateHCID 6364655Methyl (E)-4-Chloro-3-methoxy-2-butenoateHCID 10942334Sodium Methoxide2×

Produkt 1

HCID 114368685,5-bis(methoxycarbonyl)-3-methoxy-2E-pentenoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

66 g (0.5 mol) of malonic acid dimethyl ester was placed in 250 ml of N,N'-dimethylformamide. 27.8 g (0.5 mol) of sodium methylate was added at 20° C.; 10 minutes later 41.6 g (0.25 mol) of 4-chloro-3-methoxy-2E-butenoic acid methyl ester was added within 5 minutes. It was stirred for 2 hours at 20° C. Then 10.8 g (0.2 mol) of sodium methylate was added once more. After stirring for 15 hours at 20° C. it was distilled off. After working up according to Example (a) 53.8 g (81 percent) of the title compound, with a purity of 98 percent (GC), was obtained. Data for the title compound was:

Aufarbeitung

  1. stirringAfter stirring for 15 hours at 20° C. it
  2. distillationwas distilled off
  3. customwas obtained

Quellen und Nachweise

ORD-Eintrag
ord-ed63ff36add5402389411e01e7d6ae69
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05113012

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