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

HRID 630116Notes

Reaction equation

HRID 630116 reaction equation
[CH2:1]([N:3]1[C:7]([CH:8]=[O:9])=[C:6]([CH3:10])[N:5]=[CH:4]1)[CH3:2].[BH4-].[Na+].O>CO>[CH2:1]([N:3]1[C:7]([CH2:8][OH:9])=[C:6]([CH3:10])[N:5]=[CH:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 595894631-ethyl-4-methyl-1H-imidazole-5-carbaldehyde

Product 1

HCID 59589441(1-ethyl-4-methyl-1H-imidazol-5-yl)methanolYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 0° C. solution of 1-ethyl-4-methyl-1H-imidazole-5-carbaldehyde (806 mg, 5.8 mmol) in anhydrous methanol (55 mL) was added sodium borohydride (500 mg, 13.2 mmol). The reaction mixture was stirred at room temperature overnight. Water (30 mL) was added. The mixture was evaporated. The resultant residue was treated with EtOAc (50 mL). The solution was dried over MgSO4, filtered, evaporated, and dried in vacuo, affording (1-ethyl-4-methyl-1H-imidazol-5-yl)methanol (754 mg, 93% yield). The product was used without further purification.

Workup

  1. customThe mixture was evaporated
  2. additionThe resultant residue was treated with EtOAc (50 mL)
  3. dry with materialThe solution was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customdried in vacuo

Sources & evidence

ORD record
ord-76027da78de44fdfa7c7f28522ccce54
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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