Diisobutylaluminum hydride → 5-(Hydroxymethyl)-1H-benzimidazole

HRID 398349

Reaktionsgleichung

Reaktionsgleichung von HRID 398349
C([O:3][C:4]([C:6]1[CH:14]=[CH:13][C:9]2[N:10]=[CH:11][NH:12][C:8]=2[CH:7]=1)=O)C.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[OH:3][CH2:4][C:6]1[CH:14]=[CH:13][C:9]2[N:10]=[CH:11][NH:12][C:8]=2[CH:7]=1

Komponenten

4

Edukt 2

HCID 14487Diisobutylaluminum hydrideHCID 13505555Ethyl 1H-benzimidazole-6-carboxylate

Produkt 1

HCID 135055565-(Hydroxymethyl)-1H-benzimidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a cooled (0° C.) suspension of ethyl-benzimidazole-5-carboxylate (4.76 g, 25 mmol) in CH2Cl2 (100 mL) was added a 1 M solution of DIBAL in CH2Cl2 (100 mL) and the mixture was stirred for 4 h. The reaction was quenched by the sequential addition of MeOH (8 mL), 1 M NaOH (16 mL), and 30% sodium potassium tartrate (40 mL). The mixture was warmed to RT and filtered, and the solid residue was washed with CH2Cl2. The filtrate was concentrated in vacuo to afford the title compound as a brown solid:

Aufarbeitung

  1. temperatureTo a cooled
  2. customThe reaction was quenched by the sequential addition of MeOH (8 mL), 1 M NaOH (16 mL), and 30% sodium potassium tartrate (40 mL)
  3. filtrationfiltered
  4. washthe solid residue was washed with CH2Cl2
  5. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2ed67267f49b4afa92a5a77e5d9340aa
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610692B1

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