Water → HCID 57351455, compound

HRID 2207921Notes

Reaction equation

HRID 2207921 reaction equation
[K+].[Br:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11](=[O:15])[C:12]([O-:14])=[O:13])=[CH:5][CH:4]=1.[CH3:16]I.O>CN(C)C=O>[CH3:16][O:13][C:12](=[O:14])[C:11](=[O:15])[CH:10]=[CH:9][C:6]1[CH:5]=[CH:4][C:3]([Br:2])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6328Methyl iodideHCID 74111248HCID 74111248, compound

Product 1

HCID 57351455HCID 57351455, compoundYield 30.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 4-(4-bromo-phenyl)-2-oxo-3-butenoic acid potassium salt (48.0 g, 164.0 mmol) prepared in Step 1 and methyl iodide (20.0 mL, 327.0 mmol) in N,N-dimethylformamide (250.0 mL) was stirred at 75° C. for 4 hours and then distilled water was added thereto. The reaction mixture was extracted with ethyl acetate. The extract was washed with a sodium hydrogen carbonate solution and brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5) to give 13.5 g of the titled compound as a pale yellow solid.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washThe extract was washed with a sodium hydrogen carbonate solution and brine
  3. dry with materialdried on anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a yellow liquid residue
  6. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5)

Sources & evidence

ORD record
ord-0cd9582c72c54cebafe3b4bc386a8250
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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