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

HRID 1908890Notes

Reaction equation

HRID 1908890 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>CO.[C].[Pd]>[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 76%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl (6-hydroxy-1-benzofuran-3-yl)acetate (11.4 g, 55.3 mmol) in methanol (100 mL) was added 10% palladium-carbon (50% water-containing product, 2 g), and the mixture was stirred at room temperature for 18 hr under hydrogen atmosphere (balloon pressure). The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=20:80-50:50), and the obtained solid was recrystallized from ethyl acetate-hexane to give the title compound (8.74 g, yield 76%) as colorless prisms.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=20:80-50:50)
  4. customthe obtained solid was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-bceb04b7e8c843ee9ea1f77295326f83
Source dataset
uspto-grants-2013_12
Patent number
US08598226B2

Reaction notes

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