Ethyl Acetate → Ethyl 3-oxo-3-(1-triphenylmethyl-1H-imidazol-4-yl)propionate

HRID 1087293Notes

Reaction equation

HRID 1087293 reaction equation
[C:1]1([C:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH:12]=[C:11]([C:13](OC)=[O:14])[N:10]=[CH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[C:31]([O:34][CH2:35][CH3:36])(=[O:33])[CH3:32]>C1(C)C=CC=CC=1>[O:14]=[C:13]([C:11]1[N:10]=[CH:9][N:8]([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:12]=1)[CH2:32][C:31]([O:34][CH2:35][CH3:36])=[O:33]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 10429115methyl 1-trityl-1H-imidazole-4-carboxylate

Product 1

HCID 10002468Ethyl 3-oxo-3-(1-triphenylmethyl-1H-imidazol-4-yl)propionate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

202.65 g (0.55 mol) methyl (1-triphenylmethyl-1H-imidazol-4-yl)carboxylate are dissolved in 0.8 l dry toluene at 85° C. 44 g (1.1 mol) sodium hydride (60% dispersion in mineral oil) are added. To the stirred mixture 96.92 g (1.1 mol) ethyl acetate are dropped over 2 hours. The mixture is allowed to react 16 hours at 70° C. Subsequently the toluene is removed under reduced pressure. The resulting mixture is introduced into the following step without purification. For analytical purposes a small amount of the brown oily residue is dissolved in methylene chloride, washing with aqueous ammonium chloride solution and water, drying by means of sodium sulphate and evaporation lead to an oil. Crystallization with diethyl ether and recrystallization from ethanol/diethyl ether afford the title compound as white crystals, melting point 136°-139° C.

Workup

  1. customto react 16 hours at 70° C
  2. customSubsequently the toluene is removed under reduced pressure
  3. additionThe resulting mixture is introduced into the following step without purification
  4. dissolutionFor analytical purposes a small amount of the brown oily residue is dissolved in methylene chloride
  5. washwashing with aqueous ammonium chloride solution and water
  6. dry with materialdrying by means of sodium sulphate and evaporation lead to an oil
  7. customCrystallization
  8. customwith diethyl ether and recrystallization from ethanol/diethyl ether

Sources & evidence

ORD record
ord-b2121c1251d94e318f010efb13ca9b17
Source dataset
uspto-grants-1991_07
Patent number
US05034539

Reaction notes

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