Water → 1-[(E)-4-(2-naphthyl)-3-buten-1-yl]-1H-imidazole

HRID 2229253Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2229253
[N:1]1([CH2:6][CH2:7][CH2:8][CH:9]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)O)[CH:5]=[CH:4][N:3]=[CH:2]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C(COC)OC>[CH:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:19]=[CH:20][C:11]=1/[CH:9]=[CH:8]/[CH2:7][CH2:6][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 18467047HCID 18467047, Verbindung

Produkt 1

HCID 129730871-[(E)-4-(2-naphthyl)-3-buten-1-yl]-1H-imidazoleAusbeute 26,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixture of 4-(1H-imidazol-1-yl)-1-(2-naphthyl)-1-butanol (0.450 g) and p-toluenesulfonic acid hydrate (0.589 g) in dimethoxyethane (20 ml) was refluxed for 16 hours. To the mixture was added water, then the whole was concentrated and extracted with ethyl acetate. The extract was washed with water and brine, dried and concentrated. The residue was chromatographed on silica gel (ethyl acetate-MeOH=20:1) followed by crystallization from ethyl acetate-hexane to give the titled compound (0.112 g) as a colorless powder.

Aufarbeitung

  1. temperaturewas refluxed for 16 hours
  2. concentrationthe whole was concentrated
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water and brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel (ethyl acetate-MeOH=20:1)
  8. customfollowed by crystallization from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-355e4eb836264ec1ac4080633f01fce4
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06420375B1

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