Ethyl Acetate → 5-[(E)-2-phenylethenyl]-1,2,4-oxadiazole

HRID 967754

Reaktionsgleichung

Reaktionsgleichung von HRID 967754
O[NH:2][CH:3]=[N:4][C:5](=[O:14])[CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C(O)(=O)C.O1CCOCC1>[C:8]1(/[CH:7]=[CH:6]/[C:5]2[O:14][N:2]=[CH:3][N:4]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 178520452HCID 178520452, Verbindung

Produkt 1

HCID 222913425-[(E)-2-phenylethenyl]-1,2,4-oxadiazoleAusbeute 8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22565020HOAc dioxaneLösungsmittel

Versuchsvorschrift

N-[(Hydroxyamino)methylene]-cinnamamide (850 mg, 4.5 mmol) was dissolved in acetic acid/dioxane (20 mL 1:1 v:v), and heated to reflux for 2 h. The cooled solution was made basic (pH 8) with K2CO3, and partitioned between ethyl acetate and water. The organics were dried over Na2SO4, and concentrated in vacuo. The resultant solids were triturated with hot ethyl acetate, and the soluble portion was purified by flash column chromatography on silica eluting with 2:1 hexane:ethyl acetate to afford 5-[(E)-2-phenylethenyl]-1,2,4-oxadiazole (60 mg, 8% yield) as a white powder. M.p. 53–55° C. 1H NMR (CDCl3, 300 MHz) δ8.43 (s, 1H), 7.85 (d, J=16 Hz, 1H), 7.60 (m, 2H), 7.45 (m, 3H), 7.05 (d, J=16 Hz, 1H). MS (EI ionization) 171 (M+−H).

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 2 h
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe organics were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resultant solids were triturated with hot ethyl acetate
  7. customthe soluble portion was purified by flash column chromatography on silica eluting with 2:1 hexane

Quellen und Nachweise

ORD-Eintrag
ord-6ad1428dd2c64d83a156f20351cef2f1
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06956049B1

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