Ethyl 6-(Benzyloxy)benzofuran-2-carboxylate → Ethyl 6-hydroxybenzofuran-2-carboxylate

HRID 1947471Notes

Reaction equation

HRID 1947471 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:14]=[C:13]([O:15]CC3C=CC=CC=3)[CH:12]=[CH:11][C:9]=2[CH:10]=1)=[O:5])[CH3:2]>CCOC(C)=O.CCO.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:9]=2[CH:10]=1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 57810532Ethyl 6-(Benzyloxy)benzofuran-2-carboxylate

Product 1

HCID 66786469Ethyl 6-hydroxybenzofuran-2-carboxylateYield 70.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

To a solution of 6-benzyloxy-benzofuran-2-carboxylic acid ethyl ester (8.1 g, 27 mmol) in EtOAc/EtOH (3/1, 130 mL) was added Pd/C (0.8 g). The reaction mixture was shaken in a Parr Shaker under H2 (50 psi, 12 h). The reaction mixture was filtered (Celite®), washed with EtOAC (400 mL) and EtOH (100 mL). The filtrate was concentrated and the resulting residue was purified by silica gel flash chromatography using EtOAc:hexanes (0-50%) to provide the title compound as colorless solid (3.9 g, 70%). MS (ESI): mass calcd. for C11H10O4, 206.1.0; m/z found, 207.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.50 (d, J=8.6, 1H), 7.46 (d, J=0.8, 1H), 7.25-7.23 (m, 1H), 6.90 (dd, J=8.5, 2.2, 1H), 6.12 (s, 1H), 4.57-4.30 (m, 2H), 1.49-1.31 (m, 3H).

Workup

  1. filtrationThe reaction mixture was filtered (Celite®)
  2. washwashed with EtOAC (400 mL) and EtOH (100 mL)
  3. concentrationThe filtrate was concentrated
  4. customthe resulting residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-f1f3152353d7477fbf312eb715aad784
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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