Triethylamine → 2-Cyclopropanecarbonyl-7-methoxybenzofuran-4-carboxylic Acid

HRID 1108307Notes

Reaction equation

HRID 1108307 reaction equation
Br[C:2]1[C:7]2[CH:8]=[C:9]([C:11]([CH:13]3[CH2:15][CH2:14]3)=[O:12])[O:10][C:6]=2[C:5]([O:16][CH3:17])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[C]=[O:55].[O:56]1[CH2:60]CCC1.O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:13]1([C:11]([C:9]2[O:10][C:6]3[C:7](=[C:2]([C:60]([OH:56])=[O:55])[CH:3]=[CH:4][C:5]=3[O:16][CH3:17])[CH:8]=2)=[O:12])[CH2:15][CH2:14]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 18784855(4-Bromo-7-methoxybenzofuran-2-yl)-cyclopropyl-methanoneHCID 21881883Oxolane--water (1/1)HCID 178418416HCID 178418416, compound2×

Product 1

HCID 187848532-Cyclopropanecarbonyl-7-methoxybenzofuran-4-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

To a solution of (4-bromo-7-methoxybenzofuran-2-yl)-cyclopropyl-methanone (1.0 g) in tetrahydrofuran/water (40 ml/20 ml) was added palladium acetate (76 mg), 1,3-bis(diphenylphosphino)propane (280 mg) and triethylamine (4.7 ml). The reaction mixture was heated at 90° C. under a 150 psi atmosphere of carbon monoxide for 3 days. The reaction mixture was allowed to cool to room temperature and the carbon monoxide pressure released. The tetrahydrofuran was removed in vacuo and the aqueous residue washed with ethyl acetate (2×75 ml) and acidified to pH3 with 2M hydrochloric acid. The latter was extracted with ethyl acetate (2×200 ml), the organic layer separated, dried over magnesium sulfate, filtered and concentrated in vacuo to afford the title compound as a pale yellow solid (0.76 g).

Workup

  1. customThe tetrahydrofuran was removed in vacuo
  2. washthe aqueous residue washed with ethyl acetate (2×75 ml)
  3. extractionThe latter was extracted with ethyl acetate (2×200 ml)
  4. customthe organic layer separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-766be0f9dea145f88a483f785c3d20a2
Source dataset
uspto-grants-2000_05
Patent number
US06066657

Reaction notes

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