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

HRID 1163292Notes

Reaction equation

HRID 1163292 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.[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 23938PalladiumCatalystHCID 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 on carbon (50% water wet, 2 g), and the mixture was stirred under hydrogen atmosphere (balloon pressure) at room temperature for 18 hr. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20%-50% ethyl acetate/hexane), and the obtained solid was recrystallized from ethyl acetate-hexane to give the title compound (8.74 g, yield 76%) as colorless prism crystals.

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 (20%-50% ethyl acetate/hexane)
  4. customthe obtained solid was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-636cd8adfe314151bf3a685a5a1cb1a8
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

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