Allyl iodide → HCID 22414898, compound

HRID 1721427Notes

Reaction equation

HRID 1721427 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([OH:18])[CH:13]=[CH:14][C:15]=2[CH3:17])[C:10]([CH3:20])([CH3:19])[C:9]1=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:28](I)[CH:29]=[CH2:30]>CN(C)C=O>[CH2:30]([O:18][C:12]1[CH:13]=[CH:14][C:15]([CH3:17])=[C:16]2[C:11]=1[C:10]([CH3:19])([CH3:20])[C:9](=[O:21])[N:8]2[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:29]=[CH2:28]

Participants

5

Reactant 3

HCID 11166Allyl iodideHCID 11430Potassium CarbonateHCID 22414877HCID 22414877, compound

Product 1

HCID 22414898HCID 22414898, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 11.6 g (41.2 mmol) of 1-benzyl-2,3-dihydro-4-hydroxy-3,3,7-trimethyl-1H-indol-2-one and 8.6 g (62.2 mmol) of potassium carbonate in 120 ml of N,N-dimethylformamide was added 8.3 g (49.4 mmol) of allyl iodide, and the mixture was stirred overnight at 70° C. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and dried. The solvent was evaporated and the residue was purified by column chromatography (silica gel, 7:1 mixture of n-hexane and ethyl acetate) to obtain 8.9 g (yield 67.2%) of colorless needles of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. customThe solvent was evaporated
  5. customthe residue was purified by column chromatography (silica gel, 7:1 mixture of n-hexane and ethyl acetate)

Sources & evidence

ORD record
ord-db6f05847dab4bf09d63eb9f9d3c3873
Source dataset
uspto-grants-1996_04
Patent number
US05510366

Reaction notes

Loading…