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

HRID 864474ノート

反応式

HRID 864474 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-36c04faf163c4abdbfcd872962d3f60f
出典データセット
uspto-grants-1996_10
特許番号
US05563147

反応ノート

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