Imidazole → HCID 86751265, compound

HRID 1379579Notes

Reaction equation

HRID 1379579 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C([Li])CCC.[F:11][C:12]([F:22])([F:21])[C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]=O.[CH3:23][C:24]([CH3:29])([CH3:28])[C:25](Cl)=[O:26].C1C[O:33]CC1>CCCCCC>[CH3:23][C:24]([CH3:29])([CH3:28])[C:25]([O:33][C:14]1([CH:17]=[CH:18][CH:19]=[CH:20][CH:13]1[C:12]([F:11])([F:21])[F:22])[CH2:15][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)=[O:26]

Participants

7

Reactant 5

HCID 795ImidazoleHCID 8028TetrahydrofuranHCID 62493Pivaloyl chlorideHCID 123067o-(Trifluoromethyl)benzaldehydeHCID 178418339Butyllithium

Product 1

HCID 86751265HCID 86751265, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a solution of 1.5 g of imidazole in 30 ml of THF at 0° C., 8.8 ml of a 2.5M solution of n-butyl lithium in hexane were added slowly over about 7 minutes. The reaction mixture became light yellow and cloudy. After 1.5 hours, 4.2 g of 2-trifluoromethylbenzaldehyde were added slowly at about 10° C. The reaction mixture was allowed to warm to room temperature and then stirred at room temperature over the weekend. 2.9 g of trimethylacetyl chloride were added slowly at room temperature and the mixture was stirred over the weekend. Ice was added to quench the reaction and the layers were separated. The organic layer was dried (MgSO4), filtered and concentrated. The residue was put onto a silica gel column and eluted with a 1:1 mixture of hexane:ethyl acetate to yield 1.5 g of N-(1-trimethylacetoxy-2'-trifluoromethylbenzyl)-imidazole in the form of a clear oil.

Workup

  1. stirringthe mixture was stirred over the weekend
  2. additionIce was added
  3. customto quench
  4. customthe reaction
  5. customthe layers were separated
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washeluted with a 1:1 mixture of hexane

Sources & evidence

ORD record
ord-4ee6b5144e08403cb584802b0f251f6f
Source dataset
uspto-grants-1997_09
Patent number
US05672567

Reaction notes

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