Potassium Carbonate → Methyl 5-[3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoate

HRID 1019054Notes

Reaction equation

HRID 1019054 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:48]=[CH:47][C:14]([CH2:15][CH2:16][C:17]2[CH:42]=[CH:41][C:20]([CH2:21][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:19][C:18]=2[C:43]([O:45][CH3:46])=[O:44])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[N:1]1([CH2:6][CH:7]=[CH:21][C:20]2[CH:41]=[CH:42][C:17]([CH2:16][CH2:15][C:14]3[CH:13]=[CH:12][C:11]([F:10])=[CH:48][CH:47]=3)=[C:18]([CH:19]=2)[C:43]([O:45][CH3:46])=[O:44])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 222385812-(1H-Imidazol-1-yl)acetaldehydeHCID 865903414-(4-Fluorophenethyl)-3-methoxycarbonylbenzyl triphenylphosphonium bromide

Product 1

HCID 53807049Methyl 5-[3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoateYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(imidazol-1-yl)acetaldehyde (2.8 g; 0.021 mmol), 4-(4-fluorophenethyl)-3-methoxycarbonylbenzyl triphenylphosphonium bromide (6.2 g; 0.01 mmol), potassium carbonate (2.8 g; 0.02 mmol) and 18 crown-6 (0.1 g; 0.37 mmol) in dichloromethane (100 ml) was stirred under argon atmosphere at ambient temperature overnight. After extraction and evaporation to dryness, the residue was purified by flash chromatography eluting with a mixture of dichloromethane/ethanol (98/2) to give methyl 5-[3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoate as a mixture of E and Z isomers.

Workup

  1. extractionAfter extraction 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-2a2c2153a99e4eeb8073a02dd1695283
Source dataset
uspto-grants-2002_11
Patent number
US06486156B1

Reaction notes

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