Methyl acetoacetate → Dimethyl 2,6-dimethyl-4-(2-ethenylphenyl)-1,4-dihydropyridine-3,5-dicarboxylate

HRID 279868

Reaktionsgleichung

Reaktionsgleichung von HRID 279868
[CH:1]([C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O)=[CH2:2].[NH2:11]/[C:12](/[CH3:18])=[CH:13]\[C:14]([O:16][CH3:17])=[O:15].[C:19]([O:25][CH3:26])(=[O:24])[CH2:20][C:21]([CH3:23])=O.CCCCCC>CO.C(OCC)C>[CH3:18][C:12]1[NH:11][C:21]([CH3:23])=[C:20]([C:19]([O:25][CH3:26])=[O:24])[CH:5]([C:4]2[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=2[CH:1]=[CH2:2])[C:13]=1[C:14]([O:16][CH3:17])=[O:15]

Komponenten

7

Edukt 4

HCID 7757Methyl acetoacetateHCID 8058HexaneHCID 39391Benzaldehyde, 2-ethenyl-HCID 643918Methyl 3-aminocrotonate

Produkt 1

HCID 13449179Dimethyl 2,6-dimethyl-4-(2-ethenylphenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To the Compound 2a (106 mmol) in anhydrous methanol (100 ml) was added methyl 3-aminocrotonate (106 mmol) and methyl acetoacetate (106 mmol) and the resulting solution heated at reflux under nitrogen for 4 days. The solvent was removed in vacuo to give a viscous yellow oil which was diluted in diethyl ether (75 ml) and then hexane (50 ml). After stirring overnight, a yellow solid was collected by filtration and purified by flash chromatography on silica gel eluted with hexane:diethyl ether (1:2) to give Compound 2b as a yellow solid (Rf =0.4, m.p. 140°-148°).

Aufarbeitung

  1. temperaturethe resulting solution heated
  2. temperatureat reflux under nitrogen for 4 days
  3. customThe solvent was removed in vacuo
  4. customto give a viscous yellow oil which
  5. filtrationa yellow solid was collected by filtration
  6. custompurified by flash chromatography on silica gel
  7. washeluted with hexane:diethyl ether (1:2)

Quellen und Nachweise

ORD-Eintrag
ord-1847d5783e33460a9a45827d38f414b7
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04587253

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