methyl (E)-2-bromomethyl-beta-methoxycinnamate → methyl (E)-beta-methoxy-2-(4-phenyl-2-thiazolyloxymethyl)cinnamate

HRID 1735702Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1735702
[OH:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[CH3:13][O:14]/[C:15](/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27]Br)=[CH:16]/[C:17]([O:19][CH3:20])=[O:18]>CN(C=O)C.C(=O)([O-])[O-].[Ag+2]>[CH3:13][O:14]/[C:15](/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][O:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1)=[CH:16]/[C:17]([O:19][CH3:20])=[O:18]

Komponenten

5

Edukt 2

HCID 11219857methyl (E)-2-bromomethyl-beta-methoxycinnamateHCID 178517449HCID 178517449, Verbindung

Produkt 1

HCID 86749648methyl (E)-beta-methoxy-2-(4-phenyl-2-thiazolyloxymethyl)cinnamateAusbeute 56,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418647HCID 178418647, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1.2 g (0.007 mol) of 2-hydroxy-4-phenylthiazole, 2.1 g (0.0077 mol) of silver carbonate and 2.1 g (0.0074 mol) of methyl (E)-β-methoxy-2-bromomethylcinnamate (see Example 2) are stirred in 15 ml of DMF at 60° C. for 8 hours. The precipitate is filtered off and the DMF solution is poured into 100 ml of water, and the mixture is extracted with methyl tert-butyl ether. Drying and concentration of the organic phase result in a brown oil which is chromatographed on silica gel with cyclohexane/acetone (95:5). 1.5 g (56% yield) of methyl (E)-β-methoxy-2-(4-phenyl-2-thiazolyloxymethyl)cinnamate as yellowish oil are isolated as the main fraction.

Aufarbeitung

  1. filtrationThe precipitate is filtered off
  2. additionthe DMF solution is poured into 100 ml of water
  3. extractionthe mixture is extracted with methyl tert-butyl ether
  4. customDrying
  5. customconcentration of the organic phase result in a brown oil which
  6. customis chromatographed on silica gel with cyclohexane/acetone (95:5)

Quellen und Nachweise

ORD-Eintrag
ord-eafe3c5976c948ffad0f0ea1f2942595
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05538940

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