2-Pyridinecarboxaldehyde → Methyl 3-(2-pyridyl)-2-propenoate

HRID 54996

Reaktionsgleichung

Reaktionsgleichung von HRID 54996
C1(P(=[CH:20][C:21]([O:23][CH3:24])=[O:22])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH:31]=O>C(Cl)Cl>[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH:31]=[CH:20][C:21]([O:23][CH3:24])=[O:22]

Komponenten

4

Edukt 2

HCID 142732-PyridinecarboxaldehydeHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester

Produkt 1

HCID 53733726Methyl 3-(2-pyridyl)-2-propenoateAusbeute 80,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of methyl triphenylphosphoranylideneacetate (31.2 g) in CH2Cl2 (120 mL) was added dropwise over 15 minutes 2-pyridine carboxaldehyde (8.9 mL, 0.093 mol) in CH2Cl2 (40 mL). The mixture was heated to reflux for 8 hours, additional ylide (3.1 g) was added and the mixture was refluxed overnight. The reaction mixture was cooled, concentrated to 1/2 value and allowed to stand for 2 hours. A solid was collected by filtration and was washed with CH2Cl2 /hexane. The filtrate was concentrated in vacuo and the residue was vacuum distilled at 80°-107° C. and 1.5 mm Hg to afford 12.2 g (80%) of methyl 3-(2-pyridyl)-2-propenoate.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 8 hours
  3. additionadditional ylide (3.1 g) was added
  4. temperaturethe mixture was refluxed overnight
  5. temperatureThe reaction mixture was cooled
  6. concentrationconcentrated to 1/2 value
  7. filtrationA solid was collected by filtration
  8. washwas washed with CH2Cl2 /hexane
  9. concentrationThe filtrate was concentrated in vacuo
  10. distillationdistilled at 80°-107° C.

Quellen und Nachweise

ORD-Eintrag
ord-0becc70962444437964acb09faf98dd9
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624922

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