Allyl iodide → HCID 22414817, compound

HRID 1721423Notes

Reaction equation

HRID 1721423 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[C:4]([CH3:14])([CH3:13])[C:5](=[O:12])[NH:6]2.[CH2:15](I)[CH:16]=[CH2:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:17]([O:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[C:4]([CH3:14])([CH3:13])[C:5](=[O:12])[NH:6]2)[CH:16]=[CH2:15]

Participants

5

Reactant 3

HCID 11166Allyl iodideHCID 11430Potassium CarbonateHCID 22414846HCID 22414846, compound

Product 1

HCID 22414817HCID 22414817, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

8.21 g (42.99 mmol) of 2,3-dihydro-4-hydroxy-3,3,7-trimethyl-1H-indol-2-one and 7.95 g (47.3 mmol) of allyl iodide were dissolved in 65 ml of N,N-dimethylformamide. After the addition of 12.0 g (87 mmol) of potassium carbonate, the mixture was stirred for 2 hours over a water bath at 70° C. After the reaction, the solvent was removed by evaporation under reduced pressure. Chloroform was added to the residue, and the mixture was washed with water, 2N sodium hydroxide aqueous solution, and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue obtained was purified by column chromatography (silica gel, 10:1 mixture of chloroform and ethyl acetate) and crystallized from n-hexane to obtain 5.67 g (yield, 57.1%) of colorless crystals of the title compound.

Workup

  1. customAfter the reaction
  2. customthe solvent was removed by evaporation under reduced pressure
  3. additionChloroform was added to the residue
  4. washthe mixture was washed with water, 2N sodium hydroxide aqueous solution, and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customwas purified by column chromatography (silica gel, 10:1 mixture of chloroform and ethyl acetate)
  9. customcrystallized from n-hexane
  10. customto obtain

Sources & evidence

ORD record
ord-c9833d1524e24c4b8d27cf71747a22ce
Source dataset
uspto-grants-1996_04
Patent number
US05510366

Reaction notes

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