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Isopropanol → 5-Ethoxycarbonyl-3-isopropoxycarbonyl-1,4-dihydro-2,6-dimethyl-4-(3-ethynylphenyl)pyridine

HRID 467127
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 467127
[C:1]([C:3]1[CH:4]=C([CH:8]=[CH:9][CH:10]=1)C=O)#[CH:2].[C:11]([O:17][CH:18]([CH3:20])[CH3:19])(=[O:16])[CH2:12][C:13]([CH3:15])=O.[NH2:21]/[C:22](/[CH3:29])=[CH:23]\[C:24]([O:26][CH2:27][CH3:28])=[O:25].[CH:30](O)(C)[CH3:31]>N1CCCCC1>[CH2:27]([O:26][C:24]([C:23]1[CH:13]([C:15]2[CH:8]=[CH:9][CH:10]=[C:3]([C:1]#[CH:2])[CH:4]=2)[C:12]([C:11]([O:17][CH:18]([CH3:20])[CH3:19])=[O:16])=[C:30]([CH3:31])[NH:21][C:22]=1[CH3:29])=[O:25])[CH3:28]
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Komponenten

6

Edukt 4

HCID 3776IsopropanolHCID 68329Isopropyl acetoacetateHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 27716443-Ethynylbenzaldehyde

Produkt 1

HCID 198134055-Ethoxycarbonyl-3-isopropoxycarbonyl-1,4-dihydro-2,6-dimethyl-4-(3-ethynylphenyl)pyridineAusbeute 58,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8082PiperidineKatalysator

Versuchsvorschrift

To a mixture of 0.65 g (0.005 mol) of 3ethynylbenzaldehyde, 1.08 g (0.0075 mol) of isopropyl acetoacetate and 25 ml of isopropyl alcohol were added 2 to 3 drops of piperidine. After heating the mixture under reflux for 24 hours, 0.65 g (0.005 mol) of ethyl 3-aminocrotonate was added thereto, further the admixture was heated under reflux for 24 hours. After completing the reaction, the reaction mixture was concentrated. The obtained precipitate was purified by subjecting to silica gel column chromatography [eluent: n-hexane to n-hexane: ethyl acetate (7 : 3)] to give 1.1 g of the desired compound (yield: 58.6%).

Aufarbeitung

  1. temperatureAfter heating the mixture
  2. temperatureunder reflux for 24 hours
  3. temperaturefurther the admixture was heated
  4. temperatureunder reflux for 24 hours
  5. customthe reaction
  6. concentrationthe reaction mixture was concentrated
  7. customThe obtained precipitate was purified

Quellen und Nachweise

ORD-Eintrag
ord-d00579241cd841498e28cdd9874272dc
Quelldatensatz
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05158963

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