Potassium Carbonate → HCID 67015805, compound

HRID 1888729Notes

Reaction equation

HRID 1888729 reaction equation
F[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C(=O)([O-])[O-].[K+].[K+].[SH:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH:28]([CH2:33][CH3:34])[CH2:29][CH2:30][CH2:31][CH3:32])=[O:25]>CN(C=O)C.C(OCC)(=O)C>[CH2:33]([CH:28]([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:27][O:26][C:24](=[O:25])[CH2:23][CH2:22][S:21][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13])[CH3:34]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 926402-Ethylhexyl 3-mercaptopropionateHCID 5219721Methyl 4-fluoro-3-nitrobenzoate

Product 1

HCID 67015805HCID 67015805, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of methyl 4-fluoro-3-nitrobenzoate (10.0 g, 50.2 mmol) and potassium carbonate (13.9 g, 100 mmol) in DMF (120 mL) was added dropwise under ice-cooling 2-ethylhexyl 3-sulfanylpropanoate (12.1 g, 55.2 mmol), and the mixture was stirred at room temperature for 3 hr. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with water, 10% aqueous potassium carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. This solution was applied to basic silica gel column chromatography (ethyl acetate). The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1 to 3:1) to give the title compound (20.0 g, quantitative).

Workup

  1. additionwas added dropwise under ice-
  2. washthe mixture was washed with water, 10% aqueous potassium carbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1 to 3:1)

Sources & evidence

ORD record
ord-02e43a899a4c4d0497daa9cc6e2d3879
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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