Reaktion #334275

Reaktionsgleichung

1-methyl-2-chloroethyl α-acetyl-3-nitrocinnamate

methyl 3-aminocrotonate

→

title compound

Ausbeute 64.1%

methyl 1-methyl-2-chloroethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3,5-dicarboxylate

Ausbeute 64.1%

Lösungsmittel

diethyl ether

isopropanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared
2. 2
   Temperaturwas refluxed
3. 3
   TemperaturAfter cooling
4. 4
   Sonstigethe reaction mixture was evaporated to dryness under vacuum
5. 5
   Sonstigethe oil thus obtained
6. 6
   Sonstigewas chromatographed on silica gel (200 g)
7. 7
   SonstigeEvaporating the fractions
8. 8
   workup.ADDITIONcontaining a sole product (TLC, chloroform: ethylacetate 95:5)
9. 9
   Sonstigegave a thick oil, which
10. 10
    SonstigeThe solvent was then evaporated off at 20°-25° C.

Vorschrift

A solution comprising 18.72 g of 1-methyl-2-chloroethyl α-acetyl-3-nitrocinnamate, prepared as described in Example 1, and 7.12 g of methyl 3-aminocrotonate in 48 ml of isopropanol was refluxed under stirring for 210 minutes. After cooling, the reaction mixture was evaporated to dryness under vacuum and the oil thus obtained was chromatographed on silica gel (200 g) using chloroform as eluent. Evaporating the fractions containing a sole product (TLC, chloroform: ethylacetate 95:5) gave a thick oil, which was dissolved in diethyl ether. The solvent was then evaporated off at 20°-25° C. to give 15.75 g of the title compound, m.p. 95°-102° C., which could be employed without further purification.

Quelle