Sodium hydride → HCID 22664994, compound

HRID 392571Notes

Reaction equation

HRID 392571 reaction equation
[CH2:1]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14][CH2:15][O:16][CH3:17])[CH:11]=2)[C:6]1=[O:18])[CH2:2][CH2:3][CH3:4].[H-].[Na+].Br[CH2:22][CH2:23][CH2:24][CH:25]=[CH2:26]>CN(C)C=O>[CH2:1]([C:5]1([CH2:26][CH2:25][CH2:24][CH:23]=[CH2:22])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14][CH2:15][O:16][CH3:17])[CH:11]=2)[C:6]1=[O:18])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 707041-Pentene, 5-bromo-HCID 12045753HCID 12045753, compound

Product 1

HCID 22664994HCID 22664994, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 2-butyl-5-(methoxymethoxy)-1-indanone (1.54 g, 6.2 mmol) in anhydrous N,N-dimethylformamide (DMF, 5 mL) was added to a suspension of sodium hydride (372 mg of a 60% dispersion in mineral oil, 9.3 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. 5-Bromo-1-pentene (1.47 mL, 12.4 mmol) was then added over 5 minutes, during which time the mixture clarified. After stirring at room temperature for an additional 5 hours, the mixture was quenched with saturated NH4Cl, dried over MgSO4, filtered through a pad of silica, 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 19:1 hexanes-EtOAc. The product-containing fractions were evaporated under vacuum to afford 2-butyl-5-(methoxymethoxy)-2-(4-pentenyl)-1-indanone as an oil.

Workup

  1. washto rinse in the indanone solution),
  2. stirringAfter stirring at room temperature for an additional 5 hours
  3. customthe mixture was quenched with saturated NH4Cl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered through a pad of silica
  6. concentrationconcentrated under vacuum
  7. customto afford an oil
  8. customThe crude product was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 40S (4.0×7.0 cm) silica gel column
  9. washeluting with 19:1 hexanes-EtOAc
  10. customThe product-containing fractions were evaporated under vacuum

Sources & evidence

ORD record
ord-d87dd134419b434cb49739c4f20ff05f
Source dataset
uspto-grants-2004_10
Patent number
US06800785B1

Reaction notes

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