4-(3-Methoxyphenyl)-2,5-dihydrofuran-2-one → 4-(3-Methoxyphenyl)oxolan-2-one

HRID 8193Notes

Reaction equation

HRID 8193 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH2:13][O:12][C:11](=[O:14])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1>O1CCCC1.[Ni]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:13][O:12][C:11](=[O:14])[CH2:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 232433284-(3-Methoxyphenyl)-2,5-dihydrofuran-2-one

Product 1

HCID 693646374-(3-Methoxyphenyl)oxolan-2-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(3-methoxy-phenyl)-5H-furan-2-one, (1.9 g, 10 mmol) in tetrahydrofuran (100 mL) and is added Raney nickel (7.6 g, 50% suspension in water) the mixture is stirred under hydrogen (ambient pressure) 18 h at room temperature. The mixture is filtered through Celite® and concentrated in vacuo to yield the title compound, 1.54 g (80%), as a white crystalline solid.

Workup

  1. filtrationThe mixture is filtered through Celite®
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-538069ed8cf7470bb3d92d6da33140e4
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Reaction notes

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