Methyl 2-(6-hydroxy-1-benzofuran-3-yl)acetate → Methyl 2-(6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetate

HRID 922252Notes

Reaction equation

HRID 922252 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]2[C:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:7][O:8][C:4]=2[CH:3]=1>[Pd].CO>[OH:1][C:2]1[CH:15]=[CH:14][C:5]2[CH:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:7][O:8][C:4]=2[CH:3]=1

Participants

4

Reactant 1

HCID 20770861Methyl 2-(6-hydroxy-1-benzofuran-3-yl)acetate

Product 1

HCID 57345855Methyl 2-(6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetateYield 47.93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The obtained Methyl (6-hydroxy-1-benzofuran-3-yl)acetate (6 g, 29.13 mmol) was hydrogenated on 10% Palladium on carbon (1 g in 1 mL of water) in methanol (60 mL) under hydrogen atmosphere (20 psi) about 24 h. The catalyst was removed by filtration and the filtrate was concentrated. The residue was purified by silica gel column chromatography to give a solid (2.9 g, 47.93%).

Workup

  1. custom(20 psi) about 24 h
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ef74db1394cb4a458f02c8e1fe22c561
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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