Ethanol → ethyl (E)-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzylidenepyruvate

HRID 1857528Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1857528
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:27]=[CH:26][C:18](/[CH:19]=[CH:20]/[C:21](=[O:25])[C:22]([OH:24])=[O:23])=[CH:17][CH:16]=1.[CH2:28](O)[CH3:29].S(=O)(=O)(O)O>O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:27]=[CH:26][C:18](/[CH:19]=[CH:20]/[C:21](=[O:25])[C:22]([O:24][CH2:28][CH3:29])=[O:23])=[CH:17][CH:16]=1

Komponenten

5

Edukt 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 18546125(E)-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzylidenepyruvic acid

Produkt 1

HCID 10971201ethyl (E)-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzylidenepyruvateAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixture of (E)-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzylidenepyruvic acid (1.3 g) and ethanol (50 ml) was added conc. sulfuric acid (0.1 ml). The mixture was heated for 8 hours under reflux, then the reaction mixture was poured into water, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), followed by distilling off the solvent. The residue was subjected to a silica gel column chromatography. From the fractions eluted with ethyl acetate-hexane (1:3, v/v), ethyl (E)-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzylidenepyruvate (1,2 g, 86%) was obtained. Recrystallization from ethyl acetate-hexane gave pale yellow prisms. Melting point: 110-111° C.

Aufarbeitung

  1. temperatureThe mixture was heated for 8 hours
  2. temperatureunder reflux
  3. extractionwas subjected to extraction with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)
  6. distillationby distilling off the solvent
  7. washFrom the fractions eluted with ethyl acetate-hexane (1:3

Quellen und Nachweise

ORD-Eintrag
ord-0d94395cd15540878210a2c14754a510
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06147099

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