Tetrahydrofuran → 1-ethyl-1H-imidazole-2-carbaldehyde

HRID 1885833Notes

Reaction equation

HRID 1885833 reaction equation
[CH2:1]([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)[CH3:2].[O:8]1CCC[CH2:9]1.C([Li])CCC.CCCCCC>CN(C)C=O>[CH2:1]([N:3]1[CH:7]=[CH:6][N:5]=[C:4]1[CH:9]=[O:8])[CH3:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8058HexaneHCID 815401-Ethyl-1H-imidazoleHCID 178418339Butyllithium

Product 1

HCID 110623771-ethyl-1H-imidazole-2-carbaldehydeYield 93.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under nitrogen, a solution of 15.1 g (0.157 moles) N-ethylimidazole and 150 ml tetrahydrofuran was cooled to -40° C. Sixty-three ml 2.6M n-butyllithium in hexane (0.164 moles) was added via syringe. After fifteen minutes, 12.8 ml N,N-dimethylformamide was added and the reaction was allowed to warm to room temperature. After 18 hours the reaction was quenched with 5N hydrochloric acid. After stirring 15 minutes, the tetrahydrofuran was removed under reduced pressure. The remaining aqueous solution was basified with potassium carbonate solution and the product extracted into ethyl acetate (3×150 ml). After drying (anhydrous sodium sulfate) and concentration, 18.15 g (93.2%) of product was obtained as a pale tan oil, bp 90° C. at 12 mm.

Workup

  1. waitAfter fifteen minutes
  2. customAfter 18 hours the reaction was quenched with 5N hydrochloric acid
  3. customthe tetrahydrofuran was removed under reduced pressure
  4. extractionthe product extracted into ethyl acetate (3×150 ml)
  5. customAfter drying
  6. concentration(anhydrous sodium sulfate) and concentration

Sources & evidence

ORD record
ord-e60446569d7c41849e6114fde6a91838
Source dataset
uspto-grants-1992_09
Patent number
US05147863

Reaction notes

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