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

HRID 2408526Notes

Reaction equation

HRID 2408526 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][C:12]([OH:14])=[CH:13][C:8]=2[O:7][CH:6]=1>[Pd].CO>[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH:5]1[C:9]2[CH:10]=[CH:11][C:12]([OH:14])=[CH:13][C:8]=2[O:7][CH2:6]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)acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (6-hydroxy-benzofuran-3-yl)-acetic acid methyl ester (5.00 g), 10% palladium on carbon (0.50 g), and methanol (50 mL) is shaken under hydrogen atmosphere (3 bar) at room temperature for 3 h. The catalyst is separated by filtration and the filtrate is concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 4:1→1:1) to give the racemic title compound. Mass spectrum (ESI+): m/z=209 [M+H]+.

Workup

  1. customThe catalyst is separated by filtration
  2. concentrationthe filtrate is concentrated
  3. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 4:1→1:1)

Sources & evidence

ORD record
ord-61ecc48b6ca2432882164c0fd46be6b3
Source dataset
uspto-grants-2014_08
Patent number
US08815864B2

Reaction notes

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