Allyl iodide → 4-Allyloxy-2,3-dihydro-3,3-dimethyl-1H-indol-2-one

HRID 1721430Notes

Reaction equation

HRID 1721430 reaction equation
[CH3:1][C:2]1([CH3:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:11])[NH:4][C:3]1=[O:12].[CH2:14](I)[CH:15]=[CH2:16].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:16]([O:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[C:2]([CH3:13])([CH3:1])[C:3](=[O:12])[NH:4]2)[CH:15]=[CH2:14]

Participants

5

Reactant 3

HCID 11166Allyl iodideHCID 11430Potassium CarbonateHCID 5957464-Hydroxy-3,3-dimethyl-1,3-dihydro-indol-2-one

Product 1

HCID 224148734-Allyloxy-2,3-dihydro-3,3-dimethyl-1H-indol-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

1.01 g (5.71 mmol) of 2,3-dihydro-3,3-dimethyl-4-hydroxy-1H-indol-2-one, 1.92 g (5.99 mmol) of allyl iodide, and 1.57 g (11.4 mmol) of potassium carbonate were added to 8.73 ml of N,N-dimethylformamide, and the mixture was stirred for one hour over a water bath at 70° C. After the reaction, the solvent was evaporated and chloroform was added to the residue. The residue was then washed with water, 2N aqueous solution of sodium hydroxide, and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue obtained was purified by column chromatography (silica gel, chloroform) to obtain 914 mg (yield: 70.2%) of colorless prisms of the title compound.

Workup

  1. customAfter the reaction
  2. customthe solvent was evaporated
  3. additionchloroform was added to the residue
  4. washThe residue was then washed with water, 2N aqueous solution of sodium hydroxide, and 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, chloroform)

Sources & evidence

ORD record
ord-c5675356cdcb4f1c86f57e1364ac113a
Source dataset
uspto-grants-1996_04
Patent number
US05510366

Reaction notes

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