HCID 11788723, compound → 3-(4-Methoxyphenyl)cyclopentan-1-one

HRID 1508542Notes

Reaction equation

HRID 1508542 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:13][CH2:12][C:11](=[O:14])[CH:10]=2)=[CH:5][CH:4]=1>CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10]2)=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 11788723HCID 11788723, compound

Product 1

HCID 140909103-(4-Methoxyphenyl)cyclopentan-1-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a RT solution of 3-(4-methoxyphenyl)cyclopent-2-en-1-one (Step A) (4.68 g, 24.86 mmol) in EtOAc (100 ml) was added Pd/C (Degussa E101 NE/W, 10% dry weight, 50% water) (2.65 g, 1.243 mmol). The reaction mixture was degassed and flushed with nitrogen, then, degassed and flushed with hydrogen using a balloon. After 2 hours filtered reaction through a pad of Celite® washing with EtOAc. The filtrate was and purified by flash column chromatography on silica gel, eluting EtOAc in hexanes to afford the title compound as a racemic mixture. 1H NMR (500 MHz, CDCl3): δ 7.18 (d, J=8.5 Hz, 1H); 6.88 (d, J=8.6 Hz, 1H); 3.80 (s, 3H); 3.42-3.32 (m, 1H); 2.65 (dd, J=18.1, 7.4 Hz, 1H); 2.48-2.36 (m, 2H); 2.34-2.23 (m, 2H); 2.00-1.90 (m, 1H).

Workup

  1. customThe reaction mixture was degassed
  2. customflushed with nitrogen
  3. customdegassed
  4. customflushed with hydrogen using a balloon
  5. filtrationAfter 2 hours filtered
  6. customreaction through a pad of Celite®
  7. washwashing with EtOAc
  8. custompurified by flash column chromatography on silica gel
  9. washeluting EtOAc in hexanes

Sources & evidence

ORD record
ord-902af5b53e4e414588f1ea764bdaca23
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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