Water → 4-methyl-1-(propan-2-yl)-1H-imidazole-5-carbaldehyde

HRID 577083Notes

Reaction equation

HRID 577083 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[CH:7]=[O:8].I[CH:10]([CH3:12])[CH3:11].O>C1COCC1>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([CH:10]([CH3:12])[CH3:11])[C:6]=1[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 6362Isopropyl iodideHCID 27958875-Methyl-1H-imidazole-4-carbaldehyde

Product 1

HCID 595893604-methyl-1-(propan-2-yl)-1H-imidazole-5-carbaldehydeYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 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 2-iodopropane (4.5 mL, 45.4 mmol). The reaction mixture was stirred at room temperature overnight. Water (50 mL) was added. 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 (0-2% MeOH/DCM), affording 4-methyl-1-(propan-2-yl)-1H-imidazole-5-carbaldehyde (691 mg, 10% yield).

Workup

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

Sources & evidence

ORD record
ord-7c85aeae66754723ae7a45a70a8e373e
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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