Benzoic Acid → HCID 67267624, Verbindung

HRID 250207

Reaktionsgleichung

Reaktionsgleichung von HRID 250207
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.[C:9]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[CH2:10][C:11]([O:13][CH3:14])=[O:12].N1CCCCC1.C(O)(=O)C1C=CC=CC=1>C1C=CC=CC=1.O>[CH3:14][O:13][C:11](=[O:12])[C:10](=[CH:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[C:9]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15]

Komponenten

7

Edukt 4

HCID 243Benzoic AcidHCID 8082PiperidineHCID 103713-PyridinecarboxaldehydeHCID 2733872tert-Butyl methyl malonate

Produkt 1

HCID 67267624HCID 67267624, VerbindungAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of pyridine-3-carboxaldehyde (2.72 g), propanedioic acid, 1,1-dimethylethyl methyl ester (4.42 g), piperidine (0.173 g) and benzoic acid (0.155 g) in benzene (100 ml) was heated at reflux with removal of water to a Dean-Stark trap for 12 hours. The cooled mixture was washed with bicarbonate solution, concentrated under vacuum and the residue was purified by column chromatography, eluting with ethyl acetate-hexane (3:7) to afford racemic 2-pyridin-3-ylmethylene-malonic acid tert-butyl ester methyl ester as an oil (3.21 g).

Aufarbeitung

  1. temperaturewas heated
  2. washThe cooled mixture was washed with bicarbonate solution
  3. concentrationconcentrated under vacuum
  4. customthe residue was purified by column chromatography
  5. washeluting with ethyl acetate-hexane (3:7)

Quellen und Nachweise

ORD-Eintrag
ord-339ee568794649a79418bafe7076f999
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863305B2

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