Water → HCID 58604076, compound

HRID 2113653Notes

Reaction equation

HRID 2113653 reaction equation
[CH2:1]([C:4]1([CH2:17][CH3:18])[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:14][CH3:15])[CH:10]=2)[C:5]1=[O:16])[CH:2]=[CH2:3].C1(=O)C=CC(=[O:25])C=C1.O.Cl(O)(=O)(=O)=O>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:17]([C:4]1([CH2:1][C:2](=[O:25])[CH3:3])[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:14][CH3:15])[CH:10]=2)[C:5]1=[O:16])[CH3:18]

Participants

7

Reactant 4

HCID 962WaterHCID 4650QuinoneHCID 24247Perchloric AcidHCID 58604055HCID 58604055, compound

Product 1

HCID 58604076HCID 58604076, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of 2-allyl-2-ethyl-6-methoxy-3,4-dihydro-1(2H)-naphthalenone (931 mg, 3.82 mmol) in acetonitrile (11 mL) was treated with benzoquinone (619 mg, 5.73 mmol), palladium(II) acetate (172 mg, 0.76 mmol), water (0.56 mL, 31 mmol), and perchloric acid (70%, 0.15 mL, 1.74 mmol). The resulting mixture was stirred overnight at room temperature, then filtered through a small plug of silica gel. The filtrate was diluted with CH2Cl2, washed with water, and the aqueous phase was back-extracted with CH2Cl2. The combined organics were washed with brine, dried over MgSO4, filtered, and concentrated under vacuum to afford crude 2-ethyl-6-methoxy-2-(2-oxopropyl)-3,4-dihydro-1(2H)-naphthalenone as an orange oil.

Workup

  1. filtrationfiltered through a small plug of silica gel
  2. additionThe filtrate was diluted with CH2Cl2
  3. washwashed with water
  4. extractionthe aqueous phase was back-extracted with CH2Cl2
  5. washThe combined organics were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8f8586e6fe8944e09450874f20d33072
Source dataset
uspto-grants-2008_10
Patent number
US07432284B2

Reaction notes

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