Acetic Acid → 1-phenyl-1H-imidazole-2-carbaldehyde

HRID 2231238Notes

Reaction equation

HRID 2231238 reaction equation
[O:1]1CCC[CH2:2]1.[C:6]1([N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C([Li])CCC.C(OCC)=O.C(O)(=O)C>CCCCCC>[C:6]1([N:12]2[CH:16]=[CH:15][N:14]=[C:13]2[CH:2]=[O:1])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8025Ethyl formateHCID 8028TetrahydrofuranHCID 815951-PhenylimidazoleHCID 178418339Butyllithium

Product 1

HCID 64247011-phenyl-1H-imidazole-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To 50 ml of dry tetrahydrofuran containing 5.0 g (3.5 mmoles) of 1-phenylimidazole and cooled to -78° C. was added 13.8 ml (3.5 mmoles) of a 2.5M solution of n-butyllithium in hexane and the mixture stirred in the cold for one hour. Ethyl formate (2.8 ml, 3.5 mmoles) was then added and the mixture stirred for 80 minutes. Acetic acid (1.99 ml, 3.5 mmoles) was added and the cooling bath was removed. After stirring for 5 minutes the mixture was poured into water and the product extracted with ethyl acetate. The extracts were combined, dried over magnesium sulfate and concentrated to give 6.58 g of a pale yellow oil which solidified when triturated with a small amount of cold ether, 4.02 g.

Workup

  1. stirringthe mixture stirred for 80 minutes
  2. customthe cooling bath was removed
  3. stirringAfter stirring for 5 minutes the mixture
  4. additionwas poured into water
  5. extractionthe product extracted with ethyl acetate
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c89d79993a5944a081027ccd4944dab1
Source dataset
uspto-grants-1988_11
Patent number
US04782050

Reaction notes

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