Ethyl Acetate → 3-(4-Phenyl-1,3-oxazol-5-yl)propanoic acid

HRID 1982430Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1982430
[Na].I[CH2:3][CH2:4][C:5]1[O:9][CH:8]=[N:7][C:6]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:16]([O:19]CC)(=[O:18])C>CS(C)=O>[C:10]1([C:6]2[N:7]=[CH:8][O:9][C:5]=2[CH2:4][CH2:3][C:16]([OH:19])=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 5360545SodiumHCID 233165895-(2-Iodoethyl)-4-phenyloxazole

Produkt 1

HCID 132932803-(4-Phenyl-1,3-oxazol-5-yl)propanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel2×

Versuchsvorschrift

Sodium cyannide (1.18 g) was dissolved in dimethyl sulfoxide (40 ml) and, under stirring, a solution of 5-(2-iodoethyl)-4-phenyloxazole (6.0 g) in dimethyl sulfoxide (20 ml) was added dropwise. The mixture was stirred for 2 hours, followed by addition of ice-water and extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was then distilled off and the residual crude 4-phenyloxazole-5-propionitrile was dissolved in a mixture of ethanol (40 ml) and 2N sodium hydroxide (40 ml) and the solution was refluxed under stirring for 2 hours. The reaction mixture was concentrated, diluted with water and washed with dichloromethane. The aqueous layer was adjusted to pH 2 with hydrochloric acid and the resulting crystalline precipitate was collected by filtration and recrystallized from ethyl acetate and then from ethanol to give 4-phenyloxazole-5-propionic acid as prisms, yield 0.95 g (21.8%), m.p. 142°-143° C.

Aufarbeitung

  1. stirringThe mixture was stirred for 2 hours
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was then distilled off
  5. dissolutionthe residual crude 4-phenyloxazole-5-propionitrile was dissolved in a mixture of ethanol (40 ml) and 2N sodium hydroxide (40 ml)
  6. temperaturethe solution was refluxed
  7. stirringunder stirring for 2 hours
  8. concentrationThe reaction mixture was concentrated
  9. additiondiluted with water
  10. washwashed with dichloromethane
  11. filtrationthe resulting crystalline precipitate was collected by filtration
  12. customrecrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ae20f14f6d3a46f9acba520b042a9bb8
Quelldatensatz
uspto-grants-1986_06
Patentnummer
US04596816

Notizen zur Reaktion

Wird geladen…