Trityl chloride → 2-methyl-1-trityl-1H-imidazole-4-carbaldehyde

HRID 216320Notes

Reaction equation

HRID 216320 reaction equation
C(N(CC)CC)C.[C:8](Cl)([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)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:28][C:29]1[NH:30][CH:31]=[C:32]([CH:34]=[O:35])[N:33]=1>C(Cl)Cl>[CH3:28][C:29]1[N:30]([C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:31]=[C:32]([CH:34]=[O:35])[N:33]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178418999HCID 178418999, compound

Product 1

HCID 150519362-methyl-1-trityl-1H-imidazole-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (5.1 mL, 36.3 mmol) followed by trityl chloride (7.6 g, 27.2 mmol) were added to an ambient temperature solution of 2-methyl-1H-imidazole-4-carboxaldehyde (2 g, 18.2 mmol) in methylene chloride (20 mL). After stirring at ambient temperature overnight, the reaction was diluted with methylene chloride and washed with water and brine, dried (sodium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 30-70% ethyl acetate/hexane afforded 2-methyl-1-trityl-1H-imidazole-4-carboxaldehyde.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (sodium sulfate)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-77d7b4c5aa4f48f5b43d49e545abc6b9
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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