Potassium Carbonate → HCID 59167796, compound

HRID 1039181Notes

Reaction equation

HRID 1039181 reaction equation
[H-].[Na+].[C:3]1([C:9]2[NH:10][CH:11]=[CH:12][N:13]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:14][O:15][C:16](=[O:25])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]Br.C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[CH3:14][O:15][C:16](=[O:25])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:13]1[CH:12]=[CH:11][N:10]=[C:9]1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 695912-PhenylimidazoleHCID 11107373Methyl 8-bromooctanoate

Product 1

HCID 59167796HCID 59167796, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

Add sodium hydride (1.3 g, 42 mmol) to a mixture of 2-phenyl-1H-imidazole (5.0 g, 35 mmol), 8-bromooctanoic acid methyl ester (8.22 g, 35 mmol), potassium carbonate (5.75 g, 42 mmol), and tetra-n-butylammonium iodide (0.77 g, 2 mmol) in DMF (250 mL) at 0° C. under nitrogen. Heat the mixture to 75° C. and stir for 21 hours. Remove the solvent under reduced pressure, dissolve the residue in chloroform (200 mL), wash with water (100 mL) and brine (100 mL), and dry over sodium sulfate. Remove the solvent under reduced pressure and purify the residue by flash column chromatography on silica gel, eluting with methanol/methylene chloride (1:9), to afford 8-(2-phenylimidazol-1-yl)octanoic acid methyl ester (4.90 g, 47%).

Workup

  1. customRemove the solvent under reduced pressure
  2. dissolutiondissolve the residue in chloroform (200 mL)
  3. washwash with water (100 mL) and brine (100 mL)
  4. dry with materialdry over sodium sulfate
  5. customRemove the solvent under reduced pressure
  6. custompurify the residue by flash column chromatography on silica gel
  7. washeluting with methanol/methylene chloride (1:9)

Sources & evidence

ORD record
ord-05514de533844d2e86885577f9689279
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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