Potassium Carbonate → 2-cyclopropyl-3-methyl-3H-imidazole-4-carbaldehyde

HRID 2109224Notes

Reaction equation

HRID 2109224 reaction equation
F[B-](F)(F)F.[CH3:6][NH:7][C:8]([CH:10]1[CH2:12][CH2:11]1)=[NH:9].Br[C:14](=[CH:17]OC(C)C)[CH:15]=[O:16].C([O-])([O-])=O.[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CC#N>[CH:10]1([C:8]2[N:7]([CH3:6])[C:14]([CH:15]=[O:16])=[CH:17][N:9]=2)[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 534166342-Bromo-3-isopropoxy-propenalHCID 178484890HCID 178484890, compound

Product 1

HCID 210972742-cyclopropyl-3-methyl-3H-imidazole-4-carbaldehydeYield 34.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2.32 g (12.5 mmol) of N-methyl-cyclopropanecarboxamidine tetrafluoroborate in 4 mL of MeCN were added 2.41 g (12.5 mmol) of 2-bromo-3-isopropoxy-propenal, 5.1 g (37 mmol) of K2CO3, and 0.17 g (0.62 mmol) of 18-crown-6. The mixture was stirred at rt overnight, and then was concentrated and redissolved in EtOAc. Water was added to dissolve the salts, the layers were separated, and the aqueous phase was extracted twice with EtOAc. The combined extracts were washed with a small amount of water and brine, dried over Na2SO4, filtered, concentrated, and chromatographed (35-85% EtOAc in hexanes) to provide 646 mg of 2-cyclopropyl-3-methyl-3H-imidazole-4-carbaldehyde as a pale yellow oil.

Workup

  1. concentrationwas concentrated
  2. dissolutionredissolved in EtOAc
  3. additionWater was added
  4. dissolutionto dissolve the salts
  5. customthe layers were separated
  6. extractionthe aqueous phase was extracted twice with EtOAc
  7. washThe combined extracts were washed with a small amount of water and brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customchromatographed (35-85% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f4e274b3afd54e11b231f5a597020f92
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

Loading…