Dimethylformamide → HCID 58604055, compound

HRID 2113652Notes

Reaction equation

HRID 2113652 reaction equation
[H-].[Na+].[CH2:3]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[CH:11]=2)[C:6]1=[O:17])[CH3:4].[CH2:18](I)[CH:19]=C.[CH3:22]N(C=O)C>>[CH2:3]([C:5]1([CH2:18][CH3:19])[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[CH:11]=2)[C:6]1=[O:17])[CH:4]=[CH2:22]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11166Allyl iodideHCID 24758Sodium hydrideHCID 14214131HCID 14214131, compound

Product 1

HCID 58604055HCID 58604055, compound

Conditions

Temperature
2.5 °C

Procedure

NaH (0.31 g of a 60% dispersion in mineral oil, 7.6 mmol) was added to an ice-cold solution of 2-ethyl-6-methoxy-3,4-dihydro-1(2H)-naphthalenone (1.48 g, 7.2 mmol) in anhydrous DMF (14.4 mL). The mixture was purged with N2 and stirred at 0-5° C. for 45 minutes. Allyl iodide (1.0 mL, 10.9 mmol) was added and, after a few minutes, the cooling bath was removed. After stirring overnight at room temperature, the mixture was partitioned between EtOAc and water, and the aqueous phase was back-extracted several times with EtOAc. 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 to afford 2-allyl-2-ethyl-6-methoxy-3,4-dihydro-1(2H)-naphthalenone as an oil.

Workup

  1. customThe mixture was purged with N2
  2. customthe cooling bath was removed
  3. stirringAfter stirring overnight at room temperature
  4. customthe mixture was partitioned between EtOAc and water
  5. extractionthe aqueous phase was back-extracted several times with EtOAc
  6. washThe combined organics were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe residue was purified by Biotage™ (Charlottesville, Va.) flash chromatography

Sources & evidence

ORD record
ord-23a2ef39978d4b9fb12cf73ce57c8f3d
Source dataset
uspto-grants-2008_10
Patent number
US07432284B2

Reaction notes

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