Water → (1-ethyl-5-methyl-1H-imidazol-4-yl)methanol

HRID 630121Notes

Reaction equation

HRID 630121 reaction equation
[CH2:1]([N:3]1[C:7]([CH3:8])=[C:6]([CH:9]=[O:10])[N:5]=[CH:4]1)[CH3:2].[BH4-].[Na+].O>CO>[CH2:1]([N:3]1[C:7]([CH3:8])=[C:6]([CH2:9][OH:10])[N:5]=[CH:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 576783131-Ethyl-5-methyl-1H-imidazole-4-carbaldehyde

Product 1

HCID 54437975(1-ethyl-5-methyl-1H-imidazol-4-yl)methanolYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 0° C. solution of 1-ethyl-5-methyl-1H-imidazole-4-carbaldehyde (700 mg, 5.1 mmol) in anhydrous methanol (75 mL) was added sodium borohydride (380 mg, 10.0 mmol). The reaction mixture was stirred at room temperature for 2 hours. Water (20 mL) was added. The mixture was evaporated. The resultant residue was treated with EtOAc (30 mL) and water (5 mL). The mixture was dried over MgSO4, filtered, evaporated, and dried in vacuo, affording (1-ethyl-5-methyl-1H-imidazol-4-yl)methanol (350 mg, 49% yield). The product was used without further purification.

Workup

  1. customThe mixture was evaporated
  2. additionThe resultant residue was treated with EtOAc (30 mL) and water (5 mL)
  3. dry with materialThe mixture was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customdried in vacuo

Sources & evidence

ORD record
ord-b6e07afe32654fcd95eadb263030e776
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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