Water → 2-(1-Phenylimidazol-2-yl)ethanol

HRID 566259

Reaktionsgleichung

Reaktionsgleichung von HRID 566259
[C:1]1([N:7]2[CH:11]=[CH:10][N:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[CH2:17]1[O:19][CH2:18]1.O>O1CCCC1.CCCCCC>[C:1]1([N:7]2[CH:11]=[CH:10][N:9]=[C:8]2[CH2:17][CH2:18][OH:19])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 6354Ethylene OxideHCID 815951-PhenylimidazoleHCID 178418339Butyllithium

Produkt 1

HCID 212657882-(1-Phenylimidazol-2-yl)ethanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

1-Phenylimidazole (3.00 g) was dissolved in tetrahydrofuran. To the solution was added dropwise a solution of n-butyllithium (1.6 M) in hexane (16.9 ml) at −70° C. The mixture was stirred for 30 minutes at the same temperature, to which 50% solution (4.76 g) of ethyleneoxide in tetrahydrofuran. The mixture was warmed up to room temperature over 1 hour, and stirred 19 hours at the same temperature. To the reaction mixture was added water. The mixture was subjected to extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was subjected to column chromatography on silica gel (developing solvent: ethyl acetate-methanol 100:0→93:7) to give the title compound.

Aufarbeitung

  1. extractionThe mixture was subjected to extraction with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationfollowed by concentration under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d006f90833324f769be06f53a13192b2
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06174877B1

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