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

HRID 1350719Notes

Reaction equation

HRID 1350719 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-d0f1290f7eb1479381077a5011778884
Source dataset
uspto-grants-2007_05
Patent number
US07214802B2

Reaction notes

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