Trityl chloride → 4-(2,2-dimethylbut-3-en-1-yl)-1-trityl-1H-imidazole

HRID 216351Notes

Reaction equation

HRID 216351 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]([CH3:38])([CH:36]=[CH2:37])[CH2:30][C:31]1[N:32]=[CH:33][NH:34][CH:35]=1.[Cl-].[NH4+]>C(Cl)Cl>[CH3:28][C:29]([CH3:38])([CH:36]=[CH2:37])[CH2:30][C:31]1[N:32]=[CH:33][N:34]([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:35]=1

Participants

6

Reactant 4

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 178442465HCID 178442465, compound

Product 1

HCID 591404304-(2,2-dimethylbut-3-en-1-yl)-1-trityl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (1.5 mL, 53 mmol) followed by of trityl chloride (9 g, 32 mmol) were added to a 0° C. solution of 4-(2,2-dimethylbut-3-en-1-yl)-1H-imidazole (4 g, 27 mmol) in methylene chloride (40 mL). After stirring at ambient temperature for 3 h, the reaction mixture was poured into saturated aqueous ammonium chloride and extracted with methylene chloride. The combined organic extracts were washed with brine, dried (magnesium sulfate), filtered and concentrated in vacuo. Chromatography over silica eluting with 10-40% ethyl acetate/hexane afforded the title compound.

Workup

  1. extractionextracted with methylene chloride
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c3bb28a95ff844f69ce54e4f1cca7f53
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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