Tetrahydrofuran → (2-Methyl-1H-benzimidazol-4-yl)methanol

HRID 1723110Notes

Reaction equation

HRID 1723110 reaction equation
[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11](OCC)=[O:12])[C:4]=2[N:3]=1.O1CCCC1.[AlH4-].[Li+].C(OCC)(=O)C>O>[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11][OH:12])[C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8857Ethyl AcetateHCID 28112Lithium aluminum hydrideHCID 18680979ethyl 2-methyl-1H-benzimidazole-4-carboxylate

Product 1

HCID 20026664(2-Methyl-1H-benzimidazol-4-yl)methanolYield 79.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(a-2) A cooled (0° C.) solution of 10 parts of ethyl 2-methyl-1H-benzimidazole-4-carboxylate in 45 parts of tetrahydrofuran was added dropwise to a suspension of 4 parts of lithium tetrahydroaluminate in 45 parts of tetrahydrofuran. Upon complete addition, the temperature was allowed to reach room temperature. After the addition of ethyl acetate and water, the reaction mixture was filtered over diatomaceous earth. The filtrate was evaporated, yielding 6.3 parts (79.4%) of 2-methyl-1H-benzimidazole-4-methanol as a residue (int. 66).

Workup

  1. additionUpon complete addition
  2. customto reach room temperature
  3. filtrationthe reaction mixture was filtered over diatomaceous earth
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-fdcb98520d294504a9287656ca2d82b5
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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