Ethyl Acetate → 2-Butyl-5-cyano-4-(1-hydroxy-1-methylpropyl)-1-tritylimidazole

HRID 265167Notes

Reaction equation

HRID 265167 reaction equation
C[Mg]Br.[CH2:4]([C:8]1[N:9]([C:19]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:10]([C:17]#[N:18])=[C:11]([C:13](=[O:16])[CH2:14][CH3:15])[N:12]=1)[CH2:5][CH2:6][CH3:7].[Cl-].[NH4+].[C:40](OCC)(=O)C>O1CCCC1>[CH2:4]([C:8]1[N:9]([C:19]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:10]([C:17]#[N:18])=[C:11]([C:13]([OH:16])([CH3:40])[CH2:14][CH3:15])[N:12]=1)[CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 190361902-Butyl-5-cyano-4-propionyl-1-tritylimidazoleHCID 178418573HCID 178418573, compound

Product 1

HCID 190361972-Butyl-5-cyano-4-(1-hydroxy-1-methylpropyl)-1-tritylimidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
30 °C

Procedure

5 ml of a 1M solution of methylmagnesium bromide in tetrahydrofuran were added dropwise at 10° C. under an atmosphere of nitrogen to a solution of 2 g of 2-butyl-5-cyano-4-propionyl-1-tritylimidazole (prepared as described in Preparation 15) in 36 ml of tetrahydrofuran, and the resulting mixture was stirred at 20° C. for 1 hour and subsequently at 30° C. for a further 1 hour. At the end of this time, a mixture of a saturated aqueous solution of ammonium chloride and ethyl acetate was added to the reaction mixture, which was then well shaken. The ethyl acetate layer was separated and dried over anhydrous magnesium sulfate. After the drying agent had been removed by filtration, the solvent was distilled off under reduced pressure. The residue was purified by column chromatography through silica gel, using a 1:2 by volume mixture of ethyl acetate and hexane as the eluent, to give 1.29 g of the title compound as crystals, melting at 90°-93° C.

Workup

  1. additionwas added to the reaction mixture, which
  2. stirringwas then well shaken
  3. customThe ethyl acetate layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter the drying agent had been removed by filtration
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by column chromatography through silica gel
  8. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-2526db14dae144608a136b13e7fabc4d
Source dataset
uspto-grants-1997_07
Patent number
US05646171

Reaction notes

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