Aluminium lithium hydride → (1-Cyclopropyl-2,5-dimethyl-1H-imidazol-4-yl)-methanol

HRID 8894

Reaktionsgleichung

Reaktionsgleichung von HRID 8894
C([O:3][C:4]([C:6]1[N:7]=[C:8]([CH3:15])[N:9]([CH:12]2[CH2:14][CH2:13]2)[C:10]=1[CH3:11])=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH:12]1([N:9]2[C:10]([CH3:11])=[C:6]([CH2:4][OH:3])[N:7]=[C:8]2[CH3:15])[CH2:14][CH2:13]1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 45097089Ethyl 1-cyclopropyl-2,5-dimethyl-1H-imidazole-4-carboxylate

Produkt 1

HCID 21985389(1-Cyclopropyl-2,5-dimethyl-1H-imidazol-4-yl)-methanolAusbeute 104,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Cyclopropyl-2,5-dimethyl-1H-imidazole-4-carboxylic acid ethyl ester (0.7 g, 3 mmol) was dissolved in 20 mL dry THF and cooled to 0° C. Lithium aluminum hydride (3.4 mL, 1M in THF, 3 mmol) was added dropwise and stirred for 1 h at 0° C. The reaction mixture was quenched with 0.13 ml of water, 0.13 ml of 4N sodium hydroxide and 0.4 ml of water. Sodium sulfate was added, stirred for 10 min, filtered and evaporated to dryness to obtain the desired compound as a light yellow solid (0.52 g, 93%), MS: m/e=167.4 (M+H)+.

Aufarbeitung

  1. customThe reaction mixture was quenched with 0.13 ml of water, 0.13 ml of 4N sodium hydroxide and 0.4 ml of water
  2. additionSodium sulfate was added
  3. stirringstirred for 10 min
  4. filtrationfiltered
  5. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-aa284e86cc9240c4ba4ba2f67db199c4
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091222B2

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