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

HRID 397489

Reaction equation

HRID 397489 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), 1M 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: 1H NMR (400 MHz, DMSO-d6): δ4.58 (s, 1H), 7.14 (m, 1H), 7.46 (s, 1H), 7.51 (m, 1H), 8.15 (s, 1H); HRMS (FAB) C8H9N2O calcd. 149.1723 (M+1). Found 149.1045.

Workup

  1. temperatureTo a cooled
  2. customThe reaction was quenched by the sequential addition of MeOH (8 mL), 1M 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-2b7aeb2f4d7f40889c0149c021f90d69
Source dataset
uspto-grants-2003_08
Patent number
US06610701B2

Linked notes

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