Sodium Iodide → 2-((3,3-Dimethyl)oxindolyl)ethanol

HRID 864474Notes

Reaction equation

HRID 864474 reaction equation
[CH3:1][C:2]1([CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:11].[H-].[Na+].Cl[CH2:16][CH2:17][O:18]C1CCCCO1.[I-].[Na+]>CN(C)C=O>[CH3:1][C:2]1([CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:16][CH2:17][OH:18])[C:3]1=[O:11]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 2549512-(2-Chloroethoxy)tetrahydro-2H-pyranHCID 3131003,3-Dimethyl-1,3-dihydro-indol-2-one

Product 1

HCID 158173642-((3,3-Dimethyl)oxindolyl)ethanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

3,3-Dimethyl oxindole (1.1 equivalent) was dissolved in dry dimethyl formamide. Sodium hydride (60% dispersion in mineral oil) (1.1 equivalent) was added portionwise and the mixture was stirred under nitrogen for one hour at 25° C. 2-(2-Chloroethoxy)tetrahydro-2H-pyran (1 equivalent) was added with a catalytic amount of sodium iodide. The reaction mixture was stirred under nitrogen at 70° C. for 12 hours, then the solvent was removed under reduced pressure. The resulting oil was partitioned between ethyl acetate and water. The organic phase was dried (MgSO4), filtered and evaporated to dry under reduced pressure. The resulting oil was taken up in methanol and stirred at room temperature with paratoluenesulfonic acid. After eight hours the solvent was removed and replaced with ethyl acetate. The solution was washed (×2) with saturated sodium hydrogen carbonate solution, dried (MgSO4), filtered and evaporated to dryness. Column chromatography of the resulting oil on silica gel (eluent ethyl acetate/hexane 1:1) gave 2((3,3-dimethyl)oxindolyl)ethanol.

Workup

  1. stirringThe reaction mixture was stirred under nitrogen at 70° C. for 12 hours
  2. customthe solvent was removed under reduced pressure
  3. customThe resulting oil was partitioned between ethyl acetate and water
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto dry under reduced pressure
  8. stirringstirred at room temperature with paratoluenesulfonic acid
  9. customAfter eight hours the solvent was removed
  10. washThe solution was washed (×2) with saturated sodium hydrogen carbonate solution
  11. dry with materialdried (MgSO4)
  12. filtrationfiltered
  13. customevaporated to dryness

Sources & evidence

ORD record
ord-36c04faf163c4abdbfcd872962d3f60f
Source dataset
uspto-grants-1996_10
Patent number
US05563147

Reaction notes

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