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

HRID 416160Notes

Reaction equation

HRID 416160 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>CO.[C].[Pd]>[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)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-e75aff82505e4ad29ef4ec85ef8c00cd
Source dataset
uspto-grants-2012_01
Patent number
US08088821B2

Reaction notes

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