Water → 1-ethyl-4-methyl-1H-imidazole-5-carbaldehyde

HRID 630115Notes

Reaction equation

HRID 630115 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[CH:7]=[O:8].I[CH2:10][CH3:11].O>C1COCC1>[CH2:10]([N:5]1[C:6]([CH:7]=[O:8])=[C:2]([CH3:1])[N:3]=[CH:4]1)[CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 6340IodoethaneHCID 27958875-Methyl-1H-imidazole-4-carbaldehyde

Product 1

HCID 595894631-ethyl-4-methyl-1H-imidazole-5-carbaldehydeYield 13%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 4-methyl-1H-imidazole-5-carbaldehyde (5.0 g, 45.4 mmol) in anhydrous THF (50 mL) was added diaza(1,3)bicyclo[5.4.0]undecane (DBU, 6.8 mL, 45.4 mmol), and iodoethane (3.4 mL, 45.4 mmol). The mixture was stirred at room temperature overnight. Water (50 mL) was added before the THF was evaporated. The mixture was extracted with EtOAc (1×50 mL) and 2-butanol (2×50 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo. The crude product was purified by flash chromatography (0-1% MeOH/DCM), affording 1-ethyl-4-methyl-1H-imidazole-5-carbaldehyde (806 mg, 13% yield).

Workup

  1. customwas evaporated
  2. extractionThe mixture was extracted with EtOAc (1×50 mL) and 2-butanol (2×50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customdried in vacuo
  7. customThe crude product was purified by flash chromatography (0-1% MeOH/DCM)

Sources & evidence

ORD record
ord-c62358bd86e34960842cc448a873fb72
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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