3-[2,4-Bis(methoxymethoxy)phenyl]-2-cyclopenten-1-one → (+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclopentanone

HRID 2307115Notes

Reaction equation

HRID 2307115 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:8]=[CH:7][C:6]=1[C:15]1[CH2:19][CH2:18][C:17](=[O:20])[CH:16]=1>[Pd]>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:8]=[CH:7][C:6]=1[CH:15]1[CH2:19][CH2:18][C:17](=[O:20])[CH2:16]1

Participants

3

Reactant 1

HCID 223377723-[2,4-Bis(methoxymethoxy)phenyl]-2-cyclopenten-1-one

Product 1

HCID 22337807(+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclopentanoneYield 16%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

3-[2,4-Bis(methoxymethoxy)phenyl]-2-cyclopenten-1-one (50 mg) and palladium (10 mg, 10% on carbon) were stirred under an atmosphere of hydrogen for 15 hr. The mixture was then filtered through a plug of Celite, washing with ethyl acetate, and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:1 v/v) to furnish the title compound as a colourless oil (8 mg, 16%); m/z (ES+) 583 (2M+Na)+.

Workup

  1. filtrationThe mixture was then filtered through a plug of Celite
  2. washwashing with ethyl acetate
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:1 v/v)

Sources & evidence

ORD record
ord-719b438e4c504da3bf38eb47b14fd314
Source dataset
uspto-grants-2004_12
Patent number
US06828460B2

Reaction notes

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