Water → methyl 4-[(E)-2-(4-pyridyl)vinyl]benzoate

HRID 636513

Reaktionsgleichung

Reaktionsgleichung von HRID 636513
[OH-].[Na+].[Br-].[CH3:4][O:5][C:6]([C:8]1[CH:33]=[CH:32][C:11]([CH2:12][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:10][CH:9]=1)=[O:7].[N:34]1[CH:39]=[CH:38][C:37]([CH:40]=O)=[CH:36][CH:35]=1.O>CS(C)=O>[N:34]1[CH:39]=[CH:38][C:37](/[CH:40]=[CH:12]/[C:11]2[CH:10]=[CH:9][C:8]([C:6]([O:5][CH3:4])=[O:7])=[CH:33][CH:32]=2)=[CH:36][CH:35]=1.[N:34]1[CH:39]=[CH:38][C:37](/[CH:40]=[CH:12]\[C:11]2[CH:10]=[CH:9][C:8]([C:6]([O:5][CH3:4])=[O:7])=[CH:33][CH:32]=2)=[CH:36][CH:35]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 133894-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 2764257[4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromide

Produkt 2

HCID 12006312methyl 4-[(E)-2-(4-pyridyl)vinyl]benzoateHCID 70244616methyl 4-[(Z)-2-(4-pyridyl)vinyl]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of sodium hydroxide (830 mg) in dimethylsulfoxide (100 ml) was added (4-methoxycarbonylbenzyl)triphenylphosphonium bromide (10.0 g), and after 30 minutes, 4-pyridinecarbaldehyde (2.22 g) was added thereto under ice-cooling. The mixture was stirred overnight. Water was added to the reaction mixture, and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (n-hexane—ethyl acetate) to give methyl 4-[(E)-2-(4-pyridyl)vinyl]benzoate (1.18 g) and methyl 4-[(Z)-2-(4-pyridyl)vinyl]benzoate (2.67 g).

Aufarbeitung

  1. temperatureunder ice-cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (n-hexane—ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-61dcf52438ce4715b2d32a7ba6886700
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06194396B1

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