Trityl chloride → Ethyl 5-methyl-1-(triphenylmethyl)imidazole-4-carboxylate

HRID 1458578Notes

Reaction equation

HRID 1458578 reaction equation
[H-].[Na+].[CH3:3][C:4]1[N:5]=[CH:6][NH:7][C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].[C:14](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCCC1.C(OCC)(=O)C>[CH3:3][C:4]1[N:5]([C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:6]=[N:7][C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 178470400HCID 178470400, compound

Product 1

HCID 14773935Ethyl 5-methyl-1-(triphenylmethyl)imidazole-4-carboxylateYield 10.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (900 mg, 80% oil dispersion, 30 mmol) was added in portions over 5 minutes to a stirred solution of ethyl 4-methyl-imidazole-5-carboxylate (3.85 g, 25 mmol) in dry tetrahydrofuran (100 ml) at room temperature under nitrogen. After 10 minutes, trityl chloride (8.36 g, 30 mmol) was added in one portion. After 1 h, the mixture was diluted with ethyl acetate (500 ml) and washed with water (200 ml). The washings were extracted with ethyl acetate (2×75 ml) and the combined organic solutions were dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution with hexane/ethyl acetate to give ethyl 5-methyl-1-(triphenylmethyl)imidazole-4-carboxylate (1.01 g, 10%) as a white solid.

Workup

  1. waitAfter 1 h
  2. washwashed with water (200 ml)
  3. extractionThe washings were extracted with ethyl acetate (2×75 ml)
  4. dry with materialthe combined organic solutions were dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (
  7. washgradient elution with hexane/ethyl acetate

Sources & evidence

ORD record
ord-508d85682a054910b56ce5c51fa1bdce
Source dataset
uspto-grants-1998_12
Patent number
US05852016

Reaction notes

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