Water → 4-(2-(4-Formylphenyl)ethenyl)pyridine

HRID 636515Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 636515
[N:1]1[CH:6]=[CH:5][C:4](/[CH:7]=[CH:8]/[C:9]2[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=2)=[CH:3][CH:2]=1.C(N(CC)CC)C.O>CS(C)=O>[N:1]1[CH:6]=[CH:5][C:4](/[CH:7]=[CH:8]/[C:9]2[CH:10]=[CH:11][C:12]([CH:13]=[O:14])=[CH:15][CH:16]=2)=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 8471TriethylamineHCID 70240750(4-(2-(Pyridin-4-YL)vinyl)phenyl)methanol

Produkt 1

HCID 53747304-(2-(4-Formylphenyl)ethenyl)pyridineAusbeute 70,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of 4-[(E)-2-(4-pyridyl)vinyl]benzyl alcohol (740 mg) and triethylamine (1.77 g) in dimethyl sulfoxide (3 ml) was added sulfur trioxide—pyridine complex (1.11 g) at ambient temperature, and after stirring for 4 hours, water was added thereto. The mixture was extracted with ethyl acetate, and the extract was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (chloroform—ethyl acetate) and crystallized with diisopropyl ether to give 4-[(E)-2-(4-pyridyl)vinyl]-benzaldehyde (518 mg).

Aufarbeitung

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe extract was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (chloroform—ethyl acetate)
  6. customcrystallized with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-e8e367e5e80e49d28f1041d9804717ab
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06194396B1

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