1-Benzofuran-4-carboxylic acid → 2,3-Dihydro-1-benzofuran-4-carboxylic acid

HRID 2064480Notes

Reaction equation

HRID 2064480 reaction equation
[O:1]1[C:5]2=[CH:6][CH:7]=[CH:8][C:9]([C:10]([OH:12])=[O:11])=[C:4]2[CH:3]=[CH:2]1>CCO.[Pd]>[O:1]1[C:5]2=[CH:6][CH:7]=[CH:8][C:9]([C:10]([OH:12])=[O:11])=[C:4]2[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 223241171-Benzofuran-4-carboxylic acid

Product 1

HCID 187874442,3-Dihydro-1-benzofuran-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

Benzofuran-4-carboxylic acid (30.8 mmol, M. A. Eissenstat et al. J. Med. Chem. 1995, 38, 3094-3105) is added to a suspension of Pd/C (10%, 2.00 g) in EtOH (25 mL). Additional EtOH (75 mL) is added and the mixture is stirred at RT under a hydrogen atmosphere (4 bar) for 16 h. After filtration through celite and removal of the solvents the desired product is obtained which is used without further purification. 1H-NMR (DMSO-d6): δ=3.45 (t, J=8.79 Hz, 2H); 4.55 (t, J=8.79 Hz, 2H); 6.99 (d, J=7.78 Hz, 1H); 7.21 (t, J=7.91 Hz, 1H); 7.39 (d, J=7.78 Hz, 1H); 12.9 (bs, 1H).

Workup

  1. filtrationAfter filtration
  2. customthrough celite and removal of the solvents the desired product
  3. customis obtained which
  4. customis used without further purification

Sources & evidence

ORD record
ord-449a1b64a4b44756be053cd9c75b30eb
Source dataset
uspto-grants-2012_10
Patent number
US08288429B2

Reaction notes

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