Potassium Carbonate → Methyl 4-[3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoate

HRID 1019029Notes

Reaction equation

HRID 1019029 reaction equation
[N:1]1([CH2:6][CH:7]=O)[CH:5]=[CH:4][N:3]=[CH:2]1.[Br-].[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[C:19]([CH:40]=[CH:41][C:42]=2[C:43]([O:45][CH3:46])=[O:44])[CH2:20][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[N:1]1([CH2:6][CH:7]=[CH:20][C:19]2[CH:40]=[CH:41][C:42]([C:43]([O:45][CH3:46])=[O:44])=[C:17]([C:14]3[CH:13]=[CH:12][C:11]([F:10])=[CH:16][CH:15]=3)[CH:18]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 222385812-(1H-Imidazol-1-yl)acetaldehydeHCID 865903363-(4-Fluorophenyl)-4-methoxycarbonylbenzyl triphenylphosphonium bromide

Product 1

HCID 54479740Methyl 4-[3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoateYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(imidazol-1-yl)acetaldehyde (2.6 g; 0.018 mmol), 3-(4-fluorophenyl)-4-methoxycarbonylbenzyl triphenylphosphonium bromide (5.4 g; 0.09 mmol), potassium carbonate (1.38 g; 0.01 mmol) and 18 crown-6 (0.1 g; 0.37 mmol) in THF (150 ml) was stirred under argon atmosphere at ambient temperature overnight. After filtration of the insoluble material and evaporation to dryness, the residue was purified by flash chromatography eluting with a mixture of dichloromethane/ethanol (98/2) to give methyl 4-[3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoate as a mixture of E and Z isomers. Yield: 93%.

Workup

  1. filtrationAfter filtration of the insoluble material and evaporation to dryness
  2. customthe residue was purified by flash chromatography
  3. washeluting with a mixture of dichloromethane/ethanol (98/2)

Sources & evidence

ORD record
ord-440c487169fd43bb8acbbedacfd84b9a
Source dataset
uspto-grants-2002_11
Patent number
US06486156B1

Reaction notes

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