Ethyl 4-hydroxybenzofuran-6-carboxylate → Ethyl 4-hydroxy-2,3-dihydrobenzofuran-6-carboxylate

HRID 1177078Notes

Reaction equation

HRID 1177078 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:14]=[C:13]([OH:15])[C:9]2[CH:10]=[CH:11][O:12][C:8]=2[CH:7]=1)=[O:5])[CH3:2]>C(O)(=O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[CH:14]=[C:13]([OH:15])[C:9]2[CH2:10][CH2:11][O:12][C:8]=2[CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 11344757Ethyl 4-hydroxybenzofuran-6-carboxylate

Product 1

HCID 59559879Ethyl 4-hydroxy-2,3-dihydrobenzofuran-6-carboxylateYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Pd on carbon (100 mg) was added to a solution of 4-hydroxy-benzofuran-6-carboxylic acid ethyl ester (8a) (333 mg, 1.61 mmol) in acetic acid. The mixture was stirred under H2 (50 psi) for 48 hr. The mixture was filtered through Celite and concentrated. The residue was taken into saturated aqueous NaHCO3 and extracted with EtOAc. The organic layers were dried over MgSO4 and concentrated. The residue was purified by flash column chromatography eluting with 15% EtOAc in hexanes to give a pale yellow solid (315 mg, 94% yield). 1H NMR (400 MHz, CDCl3) δ 7.16 (d, J=1.26 Hz, 1 H) 7.05 (s, 1 H) 4.65 (t, J=8.72 Hz, 2 H) 4.35 (q, J=7.07 Hz, 2 H) 3.21 (t, J=8.72 Hz, 2 H) 1.38 (t, J=7.07 Hz, 3 H); LCMS for C11H12O4 m/z 209.10 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography
  7. washeluting with 15% EtOAc in hexanes

Sources & evidence

ORD record
ord-a317aeeb32274811add9ef41c1672ec2
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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