Imidazole → HCID 13254743, compound

HRID 569708Notes

Reaction equation

HRID 569708 reaction equation
[C:1]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][C:4]([O:7][CH2:8][C:9]2([C:12]([CH3:16])([CH3:15])[CH:13]=[CH2:14])[CH2:11][O:10]2)=[CH:3][CH:2]=1.[Na].[NH:24]1[CH:28]=[CH:27][N:26]=[CH:25]1>C(O)CC>[C:1]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:6]=[CH:5][C:4]([O:7][CH2:8][C:9]([OH:10])([CH2:11][N:24]2[CH:28]=[CH:27][N:26]=[CH:25]2)[C:12]([CH3:15])([CH3:16])[CH:13]=[CH2:14])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 5360545SodiumHCID 13254742HCID 13254742, compound

Product 1

HCID 13254743HCID 13254743, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent2×

Procedure

35.3 g (0.120 mol) of 2-(biphenyl-4-yloxymethyl)-2-(3,3-dimethylprop-1-en-3-yl)-oxirane, dissolved in 80 ml of n-propanol, were added to a boiling solution of 1 g (0.012 mol) of sodium propylate and 9 g (0.132 mol) of imidazole in 50 ml of n-propanol, in the course of 5 minutes. After the solution had been boiled under reflux for two days, the solvent was distilled off under reduced pressure, the residue was taken up in a mixture of 150 ml of ethyl acetate and 100 ml of dichloromethane, and the solution was washed with three times 50 ml of water. After the organic phase had been dried over anhydrous sodium sulphate, the solution was concentrated to dryness under reduced pressure. 10 ml of ethyl acetate were added to the solid residue, and the product was filtered off. 27.2 g (62.5% of theory) of 4-(biphenyl-4-yloxymethyl)-3,3-dimethyl-4-hydroxy-5-(imidazol-1-yl)pent-1-ene were obtained in the form of colorless crystals of melting point 151° to 153° C. in this manner.

Workup

  1. temperatureunder reflux for two days
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionthe residue was taken up in a mixture of 150 ml of ethyl acetate and 100 ml of dichloromethane
  4. washthe solution was washed with three times 50 ml of water
  5. dry with materialAfter the organic phase had been dried over anhydrous sodium sulphate
  6. concentrationthe solution was concentrated to dryness under reduced pressure
  7. addition10 ml of ethyl acetate were added to the solid residue
  8. filtrationthe product was filtered off

Sources & evidence

ORD record
ord-603ed4c5ef504fb8813e1ed32b86b16c
Source dataset
uspto-grants-1988_03
Patent number
US04734126

Reaction notes

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