Nitrogen → HCID 14214131, compound

HRID 2113651Notes

Reaction equation

HRID 2113651 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2.N#N.[H-].[Na+].I[CH2:19][CH3:20]>CN(C)C=O.CCOC(C)=O>[CH2:19]([CH:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:9]1=[O:13])[CH3:20]

Participants

7

Reactant 4

HCID 947NitrogenHCID 6340IodoethaneHCID 141126-Methoxy-alpha-tetraloneHCID 24758Sodium hydride

Product 1

HCID 14214131HCID 14214131, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-methoxy-3,4-dihydro-1(2H)-naphthalenone (5.0 g, 28 mmol) in anhydrous N,N-dimethylformamide (DMF, 60 mL) was purged with N2, cooled in an ice bath, stirred, and treated with NaH (1.2 g of a 60% dispersion in mineral oil, 30 mmol). The cooling bath was removed and the mixture was stirred at room temperature for 10 minutes. The mixture was re-cooled in an ice bath, treated with iodoethane (3.35 mL, 42 mmol), and then stirred under a N2 atmosphere while gradually warming to room temperature. After stirring for 2.9 days, the mixture was diluted with EtOAc (250 mL) and washed with water (200 mL), and the aqueous phase was back-extracted with EtOAc (100 mL). The combined organics were washed with brine, dried over MgSO4, filtered, and concentrated under vacuum. The residue was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 40M (4×15 cm) silica gel column, eluting successively with 1000 mL portions of 0.2%, 1%, 2%, and 5% EtOAc in hexane. The product-containing fractions were combined and evaporated under vacuum to afford 2-ethyl-6-methoxy-3,4-dihydro-1(2H)-naphthalenone as an oil.

Workup

  1. temperaturecooled in an ice bath
  2. customThe cooling bath was removed
  3. stirringthe mixture was stirred at room temperature for 10 minutes
  4. temperatureThe mixture was re-cooled in an ice bath
  5. stirringstirred under a N2 atmosphere
  6. stirringAfter stirring for 2.9 days
  7. washwashed with water (200 mL)
  8. extractionthe aqueous phase was back-extracted with EtOAc (100 mL)
  9. washThe combined organics were washed with brine
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated under vacuum
  13. customThe residue was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 40M (4×15 cm) silica gel column
  14. washeluting successively with 1000 mL portions of 0.2%, 1%, 2%, and 5% EtOAc in hexane
  15. customevaporated under vacuum

Sources & evidence

ORD record
ord-1745c1d11fd44e5aad8ac320f4034dbc
Source dataset
uspto-grants-2008_10
Patent number
US07432284B2

Reaction notes

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