Allyl iodide → HCID 12045757, compound

HRID 2113642Notes

Reaction equation

HRID 2113642 reaction equation
[CH2:1]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14][CH3:15])[CH:11]=2)[C:6]1=[O:16])[CH2:2][CH2:3][CH3:4].[H-].[Na+].[CH2:19](I)[CH:20]=[CH2:21]>CN(C)C=O>[CH2:21]([C:5]1([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14][CH3:15])[CH:11]=2)[C:6]1=[O:16])[CH:20]=[CH2:19]

Participants

5

Reactant 3

HCID 11166Allyl iodideHCID 24758Sodium hydrideHCID 120457522-Butyl-5-methoxy-1-indanone

Product 1

HCID 12045757HCID 12045757, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 2-butyl-5-methoxy-1-indanone (500 mg, 2.3 mmol) in anhydrous N,N-dimethylformamide (DMF, 5 mL) was added to a suspension of sodium hydride (100 mg of a 60% dispersion in mineral oil, 2.5 mmol) in DMF (5 mL). The mixture was diluted with more DMF (2 mL, used to rinse in the indanone solution), placed under a nitrogen atmosphere, and stirred at room temperature for 25 minutes. Allyl iodide (0.32 mL, 3.5 mmol) was then added over 5 minutes, during which time the mixture clarified. After stirring at room temperature for an additional 15.5 hours, the mixture was partitioned between EtOAc (200 mL) and water (150 mL) containing brine. The aqueous phase was extracted with EtOAc (2×100 mL). The combined EtOAc solution was washed with brine, dried over MgSO4, filtered, and concentrated under vacuum to afford an oil. The crude product was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 40S (4.0×7.0 cm) silica gel column, eluting with 49:1 hexanes-EtOAc. The product-containing fractions were evaporated under vacuum to afford 2-allyl-2-butyl-5-methoxy-1-indanone as an oil.

Workup

  1. washto rinse in the indanone solution),
  2. stirringAfter stirring at room temperature for an additional 15.5 hours
  3. customthe mixture was partitioned between EtOAc (200 mL) and water (150 mL)
  4. additioncontaining brine
  5. extractionThe aqueous phase was extracted with EtOAc (2×100 mL)
  6. washThe combined EtOAc solution was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customto afford an oil
  11. customThe crude product was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 40S (4.0×7.0 cm) silica gel column
  12. washeluting with 49:1 hexanes-EtOAc
  13. customThe product-containing fractions were evaporated under vacuum

Sources & evidence

ORD record
ord-d9bb6cd38a26403dbc2dfd34de2237dd
Source dataset
uspto-grants-2008_10
Patent number
US07432284B2

Reaction notes

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