Citric Acid → 2-[1-(triphenylmethyl)-1H-imidazol-2-yl]acetaldehyde

HRID 1498063Notes

Reaction equation

HRID 1498063 reaction equation
C([Li])CCC.[CH3:6][C:7]1[N:8]([C:12]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:9]=[CH:10][N:11]=1.[O:31]1CCC[CH2:32]1.C(OCC)=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CCCCCC>[C:12]([N:8]1[CH:9]=[CH:10][N:11]=[C:7]1[CH2:6][CH:32]=[O:31])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 5

HCID 311Citric Acid2×HCID 8025Ethyl formateHCID 8028TetrahydrofuranHCID 6182462-Methyl-1-tritylimidazoleHCID 178418339Butyllithium

Product 1

HCID 509908112-[1-(triphenylmethyl)-1H-imidazol-2-yl]acetaldehyde

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

1.6 M of n-Butyllithium in hexane (7.5 mL) was added dropwise to a solution of 2-Methyl-1-trityl-1H-imidazole (3.244 g, 10.00 mmol) in Tetrahydrofuran (100.0 mL, 1233 mmol) at −76° C. The dark red mixture was stirred for 45 min. Ethyl formate (4.039 mL, 50.00 mmol) was added quickly and the mixture (turned yellowish) was stirred for 20 min. 6 ml of 5% aq. citric acid were added and the mixture was mixed with 60 ml of aq citric acid and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over MgSO4 and concentrated in vacuum. Pale yellow semisolid material (2.025 g, 57.5%) was used in the next step without further purification.

Workup

  1. stirringthe mixture (turned yellowish) was stirred for 20 min
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuum
  6. customPale yellow semisolid material (2.025 g, 57.5%) was used in the next step without further purification

Sources & evidence

ORD record
ord-9e59537d11e944fcbf489a5fbf29ff5d
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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