Ethyl Acetate → 2-Butyl-5-cyano-4-propionyl-1-tritylimidazole

HRID 265165Notes

Reaction equation

HRID 265165 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[CH2:5]([C:9]1[N:10]([C:18]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:11]([C:16]#[N:17])=[C:12]([C:14]#N)[N:13]=1)[CH2:6][CH2:7][CH3:8].[Cl-].[NH4+].C(OCC)(=[O:41])C>C(OCC)C.O1CCCC1>[CH2:5]([C:9]1[N:10]([C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:11]([C:16]#[N:17])=[C:12]([C:14](=[O:41])[CH2:1][CH3:2])[N:13]=1)[CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 190361382-Butyl-1-tritylimidazole-4,5-dicarbonitrileHCID 178418443HCID 178418443, compound

Product 1

HCID 190361902-Butyl-5-cyano-4-propionyl-1-tritylimidazole

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

14 ml of a 3M solution of ethylmagnesium bromide in diethyl ether were added dropwise at 10° C. under an atmosphere of nitrogen to a solution of 8.33 g of 2-butyl-1-tritylimidazole-4,5-dicarbonitrile [prepared as described in Preparation 5(i)] in 83 ml of tetrahydrofuran, and the resulting mixture was stirred at room temperature for 3 hours. 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, whilst ice-cooling. The ethyl acetate layer was separated, washed with water and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure. The crystalline product thus obtained was washed with diisopropyl ether, to give 4.56 g of the title compound, melting at 140°-143° C. (softening at 83° C.).

Workup

  1. additionwas added to the reaction mixture, whilst ice-
  2. temperaturecooling
  3. customThe ethyl acetate layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was then removed by distillation under reduced pressure
  7. customThe crystalline product thus obtained
  8. washwas washed with diisopropyl ether

Sources & evidence

ORD record
ord-9f74d61f40e449f8a929a1ea03284198
Source dataset
uspto-grants-1997_07
Patent number
US05646171

Reaction notes

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