tert-Butyl methyl ether → 1-Ethyl-2-methyl-1H-benzimidazole-5-methanol

HRID 1591972Notes

Reaction equation

HRID 1591972 reaction equation
C[O:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]2[N:9]([CH2:13][CH3:14])[C:10]([CH3:12])=[N:11][C:7]=2[CH:6]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+].CC(OC)(C)C>C1COCC1>[CH2:13]([N:9]1[C:8]2[CH:15]=[CH:16][C:5]([CH2:3][OH:2])=[CH:6][C:7]=2[N:11]=[C:10]1[CH3:12])[CH3:14]

Participants

6

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 24436Sodium SulfateHCID 699512methyl 1-ethyl-2-methylbenzimidazole-5-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 7594531-Ethyl-2-methyl-1H-benzimidazole-5-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 450 mg (2.06 mmol) of the title D compound, 1-ethyl-2-methyl-1H-benzoimidazole-5-carboxylic acid methyl ester in 5 mL of THF is added dropwise 2.1 mL (2.1 mmol) of lithium aluminum hydride (LAH, 1.0M in THF). The mixture is stirred at RT for 90 min, then saturated aqueous sodium sulfate solution is carefully added dropwise until a thick precipitate formed. MTBE is added to the mixture and the insoluble aluminum salts are removed by filtration through Celite. The solvent is removed under reduced pressure to give (1-ethyl-2-methyl-1H-benzoimidazol-5-yl)-methanol as an oil: 1H-NMR (CDCl3) δ 7.63 (s, 1H), 7.28 (m, 2H), 4.77 (s, 2H), 4.16 (q, 2H), 3.74 (t, broad, 1H), 2.60 (s, 3H), 1.40 (t, 3H); [M+1]+=191.

Workup

  1. customformed
  2. customthe insoluble aluminum salts are removed by filtration through Celite
  3. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-1dd681173da94f86af96faad29f2ec37
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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