Sodium Hydroxide → alpha(or beta)-methyl-1H-imidazole-1-ethanol

HRID 368351Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 368351
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1([CH:12]([CH3:18])[C:13](OCC)=[O:14])[CH:11]=[CH:10][N:9]=[CH:8]1.[OH-].[Na+]>C1COCC1>[N:7]1([CH:12]([CH3:18])[CH2:13][OH:14])[CH:11]=[CH:10][N:9]=[CH:8]1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 18626501ethyl 2-(1H-imidazol-1-yl)propanoateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 109147alpha(or beta)-methyl-1H-imidazole-1-ethanolAusbeute 67,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A suspension of 16.6 g (0.437 mol) of lithium aluminum hydride in 700 mL of THF was warmed to 40° C. and treated dropwise with 36.8 g (0.219 mol) of ethyl 2-(1H-1-imidazolyl)propanoate and the suspension allowed to stir at room temperature for 2.5 hours. The mixture was decomposed with dilute NaOH, filtered, and the solid washed with THF. The solvent was removed under reduced pressure and the residue distilled at 155-170° C./0.5 mm Hg. There was obtained 18.6 g (67% yield) of the product as an oil. The structure was confirmed by NMR and mass spectroscopy. MS m/z 127 (M+H+).

Aufarbeitung

  1. filtrationfiltered
  2. washthe solid washed with THF
  3. customThe solvent was removed under reduced pressure
  4. distillationthe residue distilled at 155-170° C./0.5 mm Hg

Quellen und Nachweise

ORD-Eintrag
ord-bcdbe99f28114cbfada7305cdfdbbe15
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06133303

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