Carbon Dioxide → 1-(Methoxymethyl)-alpha-phenyl-alpha-(p-trifluoromethyl-phenyl)imidazole-2-methanol

HRID 261947Notes

Reaction equation

HRID 261947 reaction equation
C([Li])CCC.[Li].C(Br)CCC.[CH3:12][O:13][CH2:14][N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1.CN(C)CCN(C)C.[F:28][C:29]([F:45])([F:44])[C:30]1[CH:43]=[CH:42][C:33]([C:34]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:35])=[CH:32][CH:31]=1.C(=O)=O>O.O1CCCC1.C(OCC)C>[CH3:12][O:13][CH2:14][N:15]1[CH:19]=[CH:18][N:17]=[C:16]1[C:34]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:33]1[CH:32]=[CH:31][C:30]([C:29]([F:45])([F:44])[F:28])=[CH:43][CH:42]=1)[OH:35]

Participants

11

Reactant 7

HCID 280Carbon DioxideHCID 8002Butyl bromideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 697674-(Trifluoromethyl)benzophenoneHCID 883591-(methoxymethyl)-1H-imidazoleHCID 3028194LithiumHCID 178418339Butyllithium

Product 1

HCID 124338961-(Methoxymethyl)-alpha-phenyl-alpha-(p-trifluoromethyl-phenyl)imidazole-2-methanol

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-65 °C

Procedure

A butyllithium solution, prepared from 1.02 g. (0.145 g. at.) of lithium and 7.9 g. (0.058 mol) of butyl bromide in 70 ml. of anhydrous diethyl ether, was added drop-wise at -60° C. to -65° C. under a nitrogen atmosphere to a solution of 4.9 g. (0.044 mol) of 1-(methoxymethyl)imidazole and 3.1 g. (0.044 mol) of N,N,N',N'-tetramethylethylenediamine in 125 ml. of anhydrous tetrahydrofuran. The reaction mixture was kept standing for 2 hours at -60° to -65° C. and then 11 g. (0.044 mol) of 4-(trifluoromethyl)benzophenone, dissolved in 75 ml. of anhydrous tetrahydrofuran, were added drop-wise. The temperature was maintained at -65° C. for one hour and then the reaction mixture was allowed to attain room temperature overnight. 10 ml. of water and solid carbon dioxide were added and the solvent was distilled off. The residue was dissolved in dilute hydrochloric acid, the solution was washed with diethyl ether and made alkaline with potassium carbonate. The solid substance formed was filtered off and dissolved in chloroform. The solution was washed with water, dried over sodium sulphate and concentrated by evaporation of the solvent. The residue was crystallised from isopropyl alcohol. 1-(Methoxymethyl)-α-phenyl-α-(p-trifluoromethyl-phenyl)imidazole-2-methanol was obtained. Melting point 158°-159° C.

Workup

  1. waitto attain room temperature overnight
  2. distillationthe solvent was distilled off
  3. dissolutionThe residue was dissolved in dilute hydrochloric acid
  4. washthe solution was washed with diethyl ether
  5. customThe solid substance formed
  6. filtrationwas filtered off
  7. dissolutiondissolved in chloroform
  8. washThe solution was washed with water
  9. dry with materialdried over sodium sulphate
  10. concentrationconcentrated by evaporation of the solvent
  11. customThe residue was crystallised from isopropyl alcohol

Sources & evidence

ORD record
ord-64f5f377bbfb4dfb8287992cb8ab85b3
Source dataset
uspto-grants-1979_05
Patent number
US04152441

Reaction notes

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