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

HRID 425319Notes

Reaction equation

HRID 425319 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-2d37aab99b334767be67b59e53888593
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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