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Ethanol → 5-Isopropoxycarbonyl-1,4-dihydro-2,6-dimethyl-3-methoxyethoxycarbonyl-4-(3-ethynylphenyl)pyridine

HRID 467123
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 467123
[C:1]([C:3]1[CH:4]=C([CH:8]=[CH:9][CH:10]=1)C=O)#[CH:2].[NH2:11]/[C:12](/[CH3:20])=[CH:13]\[C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15].[C:21]([O:27][CH2:28][CH2:29][O:30][CH3:31])(=[O:26])[CH2:22][C:23]([CH3:25])=O.[CH2:32](O)[CH3:33]>>[CH:17]([O:16][C:14]([C:13]1[CH:23]([C:25]2[CH:8]=[CH:9][CH:10]=[C:3]([C:1]#[CH:2])[CH:4]=2)[C:22]([C:21]([O:27][CH2:28][CH2:29][O:30][CH3:31])=[O:26])=[C:32]([CH3:33])[NH:11][C:12]=1[CH3:20])=[O:15])([CH3:19])[CH3:18]
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Komponenten

5

Edukt 4

HCID 702EthanolHCID 897342-Methoxyethyl acetoacetateHCID 27716443-EthynylbenzaldehydeHCID 111372742-Butenoic acid, 3-amino-, 1-methylethyl ester

Produkt 1

HCID 198134195-Isopropoxycarbonyl-1,4-dihydro-2,6-dimethyl-3-methoxyethoxycarbonyl-4-(3-ethynylphenyl)pyridineAusbeute 53 %

Versuchsvorschrift

In 30 ml of dry ethyl alcohol was dissolved 1.3 g (10 mmol) of 3-ethynylbenzaldehyde, and 1.43 g (10 mmol) of isopropyl 3-aminocrotonate and 1.6 g (10 mmol) of methoxyethyl acetoacetate were successively added thereto at room temperature. The admixture was reacted under reflux with heating for 12 hours. After completing the reaction, the reaction solution was distilled away under reduced pressure and purified by subjecting to silica gel column chromatography [eluent: n-hexane-chloroform (1 : 1) to chloroform]to give 2.1 g of the chloroform (1 : 1) to chloroform] to give 2.1 g of the desired compound (yield: 53%).

Aufarbeitung

  1. additionwere successively added
  2. customat room temperature
  3. customThe admixture was reacted
  4. temperatureunder reflux
  5. temperaturewith heating for 12 hours
  6. customthe reaction
  7. distillationthe reaction solution was distilled away under reduced pressure
  8. custompurified
  9. customto give 2.1 g of the chloroform (1 : 1) to chloroform]

Quellen und Nachweise

ORD-Eintrag
ord-d5704b7d097b4eca9c81603ae798a68b
Quelldatensatz
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05158963

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