Potassium Hydroxide → HCID 58604065, compound

HRID 2113654Notes

Reaction equation

HRID 2113654 reaction equation
[CH2:1]([C:3]1([CH2:16][C:17](=[O:19])[CH3:18])[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:13][CH3:14])[CH:9]=2)[C:4]1=O)[CH3:2].[OH-].[K+]>CCO.CCOC(C)=O>[CH2:1]([C:3]12[CH2:16][C:17](=[O:19])[CH:18]=[C:4]1[C:5]1[C:10]([CH2:11][CH2:12]2)=[CH:9][C:8]([O:13][CH3:14])=[CH:7][CH:6]=1)[CH3:2]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 58604076HCID 58604076, compound

Product 1

HCID 58604065HCID 58604065, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of crude 2-ethyl-6-methoxy-2-(2-oxopropyl)-3,4-dihydro-1(2H)-naphthalenone (758 mg, 3 mmol) in EtOH (15 mL) was treated with freshly prepared 2N KOH in EtOH (1.5 mL, 3 mmol). The resulting solution was heated at reflux for 24 hours. After cooling, the mixture was diluted with EtOAc (70 mL) and washed with 1N HCl (35 mL) followed by 5% NaHCO3 (35 mL). The NaHCO3 phase was back-extracted with EtOAc (60 mL). The combined organics were washed with water and brine, dried over MgSO4, filtered, and concentrated under vacuum. The residue was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 40 M (4×15 cm) silica gel column, eluting with 4:1 hexane-EtOAc, to provide 3a-ethyl-7-methoxy-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one as an oil.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 24 hours
  3. temperatureAfter cooling
  4. washwashed with 1N HCl (35 mL)
  5. extractionThe NaHCO3 phase was back-extracted with EtOAc (60 mL)
  6. washThe combined organics were washed with water and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe residue was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 40 M (4×15 cm) silica gel column
  11. washeluting with 4:1 hexane-EtOAc

Sources & evidence

ORD record
ord-2056d151a684402a8e7b6ebbb4bebe15
Source dataset
uspto-grants-2008_10
Patent number
US07432284B2

Reaction notes

Loading…