Water → (1-ethyl-4-methyl-1H-imidazol-5-yl)methanol
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
Product 1
Reagents, catalysts & solvents 1
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
- customThe mixture was evaporated
- additionThe resultant residue was treated with EtOAc (50 mL)
- dry with materialThe solution was dried over MgSO4
- filtrationfiltered
- customevaporated
- customdried in vacuo
Sources & evidence
- ORD record
- ord-76027da78de44fdfa7c7f28522ccce54
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315521B2
Reaction notes
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