Triethylamine → 3-[(1E)-3-ethoxy-3-oxoprop-1-en-1-yl]benzoic acid

HRID 2041973Notes

Reaction equation

HRID 2041973 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[CH:12]=[CH2:13].C(N(CC)CC)C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:16]([O:15][C:11](=[O:14])/[CH:12]=[CH:13]/[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6])[CH3:17]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 120603-Iodobenzoic acid

Product 1

HCID 104890843-[(1E)-3-ethoxy-3-oxoprop-1-en-1-yl]benzoic acidYield 104.3%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-iodobenzoic acid (20.2 g, 81.4 mmol), ethyl acrylate (9.0 g, 90.2 mmol), triethylamine (24 mL) and palladium acetate (92 mg, 0.41 mmol) in DMF (130 mL) was stirred at 140° C. for 3 hr. The reaction mixture was cooled to room temperature, partitioned between ethyl acetate and 1N hydrochloric acid, and the ethyl acetate layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate 50:50-0:100) to give the title compound (18.7 g, quant.) as an orange solid.

Workup

  1. custompartitioned between ethyl acetate and 1N hydrochloric acid
  2. washthe ethyl acetate layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate 50:50-0:100)

Sources & evidence

ORD record
ord-c6e8a7db4a024229ae59b78527dc5c8b
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

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