Potassium Carbonate → (Z)-4-[4-(2-Imidazol-1-yl-ethoxy)phenyl]-3,4-diphenyl-but-3-en-1-ol

HRID 1368937Notes

Reaction equation

HRID 1368937 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8](/[C:11](/[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:12](\[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)/[CH2:13][CH2:14][OH:15])=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[Na].[NH:35]1[CH:39]=[CH:38][N:37]=[CH:36]1>C(C(C)=O)C>[N:35]1([CH2:2][CH2:3][O:4][C:5]2[CH:10]=[CH:9][C:8](/[C:11](/[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:12](\[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)/[CH2:13][CH2:14][OH:15])=[CH:7][CH:6]=2)[CH:39]=[CH:38][N:37]=[CH:36]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 57373095Imidazole sodiumHCID 69544510Z-1,2-diphenyl-1-[4-(bromoethoxy)phenyl]-1-buten-4-ol

Product 1

HCID 69545262(Z)-4-[4-(2-Imidazol-1-yl-ethoxy)phenyl]-3,4-diphenyl-but-3-en-1-ol

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

(Z)-4-[4-(2-Bromoethoxy)phenyl]-3,4-diphenylbut-3-en-1-ol (preparation described in U.S. Pat. No. 4,996,225) (4.97 g, 0.0117 mol) is dissolved in methyl ethyl ketone (50 ml) and potassium carbonate (4.8 g, 0.035 mol) and imidazole sodium salt (2.1 1 g, 0.0234 mol) is added to the solution. Mixture is stirred and refluxed for five hours. Then the solution is filtered and the filtrate is evaporated to dryness. The residue is dissolved in ethyl acetate, washed with 2 N aqueous sodium hydroxide solution and with water, dried and evaporated to dryness. The residue is recrystallized from the mixture of toluene and acetonitrile.

Workup

  1. temperaturerefluxed for five hours
  2. filtrationThen the solution is filtered
  3. customthe filtrate is evaporated to dryness
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. washwashed with 2 N aqueous sodium hydroxide solution and with water
  6. customdried
  7. customevaporated to dryness
  8. customThe residue is recrystallized from the mixture of toluene and acetonitrile

Sources & evidence

ORD record
ord-09aec0aefdfa4d7382da0b1871bcd746
Source dataset
uspto-grants-2003_06
Patent number
US06576645B1

Reaction notes

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