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

HRID 398349

Reaction equation

HRID 398349 reaction equation
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

Participants

4

Reactant 2

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

Product 1

HCID 135055565-(Hydroxymethyl)-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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:

Workup

  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

Sources & evidence

ORD record
ord-2ed67267f49b4afa92a5a77e5d9340aa
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Linked notes

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