Water → 2-butyl-6-methoxy-2-(2-oxopropyl)-3,4-dihydro-1(2H)-naphthalenone

HRID 2113660Notes

Reaction equation

HRID 2113660 reaction equation
[CH2:1]([C:4]1([CH2:17][CH2:18][CH2:19][CH3:20])[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:27])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:27])[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])[CH2:18][CH2:19][CH3:20]

Participants

7

Reactant 4

HCID 962WaterHCID 4650QuinoneHCID 24247Perchloric AcidHCID 586040462-allyl-2-butyl-6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 586040662-butyl-6-methoxy-2-(2-oxopropyl)-3,4-dihydro-1(2H)-naphthalenone

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of 2-allyl-2-butyl-6-methoxy-3,4-dihydro-1(2H)-naphthalenone (931 mg, 3.4 mmol) in acetonitrile (10 mL) was treated with benzoquinone (553 mg, 5.12 mmol), palladium(II) acetate (155 mg, 0.69 mmol), water (0.50 mL, 28 mmol), and perchloric acid (70%, ˜0.14 mL, 1.6 mmol). The resulting mixture was stirred overnight at room temperature. The mixture was partitioned between CH2Cl2 (200 mL) and water (100 mL) and the aqueous phase was back-extracted with CH2Cl2 (2×75 mL). The combined organics were washed with brine, dried over MgSO4, filtered, and concentrated under vacuum. The residue (1.17 g) was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 40S (4×7 cm) silica gel column, eluting with 10:1 to 5:1 hexane-EtOAc. The product-containing fractions were evaporated under vacuum to afford 2-butyl-6-methoxy-2-(2-oxopropyl)-3,4-dihydro-1(2H)-naphthalenone as an oil.

Workup

  1. customThe mixture was partitioned between CH2Cl2 (200 mL) and water (100 mL)
  2. extractionthe aqueous phase was back-extracted with CH2Cl2 (2×75 mL)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue (1.17 g) was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 40S (4×7 cm) silica gel column
  8. washeluting with 10:1 to 5:1 hexane-EtOAc
  9. customThe product-containing fractions were evaporated under vacuum

Sources & evidence

ORD record
ord-787cfc2492bd47d0ae9c3bf3d14a5fd4
Source dataset
uspto-grants-2008_10
Patent number
US07432284B2

Reaction notes

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