1,3-Dichloroacetone → 4-Chloromethyl-2-styryl-oxazole

HRID 1584326

Reaktionsgleichung

Reaktionsgleichung von HRID 1584326
[C:1]([NH2:11])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:12][CH2:13][C:14]([CH2:16]Cl)=O.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:12][CH2:13][C:14]1[N:11]=[C:1](/[CH:2]=[CH:3]/[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[O:10][CH:16]=1

Komponenten

5

Edukt 3

HCID 107931,3-DichloroacetoneHCID 11430Potassium CarbonateHCID 121352-Propenamide, 3-phenyl-

Produkt 1

HCID 220097524-Chloromethyl-2-styryl-oxazoleAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of cinnamamide (25.3 g) and 1,3-dichloroacetone (20.9 g) was heated for one hour at 130° C. The reaction mixture was poured into water, which was neutralized with potassium carbonate, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The concentrate was purified by column chromatography on silica gel. From the fraction eluted with ether-hexane (1:5, v/v), was obtained 4-chloromethyl-2-[(E)-styryl] oxazole (16.9 g, 47%), which was recrystallized from ether-hexane to yield colorless needless, m.p.72-73° C.

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe concentrate was purified by column chromatography on silica gel
  6. washFrom the fraction eluted with ether-hexane (1:5

Quellen und Nachweise

ORD-Eintrag
ord-c13f1359046844c7ae845f82660227f3
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05932601

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