Sodium Iodide → 2-(2-Hydroxyisobutyl)-Phthalimide

HRID 2369458

反応式

HRID 2369458 の反応式
Cl[CH2:2][C:3]([CH3:6])([OH:5])[CH3:4].[C:7]1(=[O:17])[NH:11][C:10](=[O:12])[C:9]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:8]12.[K].[I-].[Na+]>CN(C=O)C>[OH:5][C:3]([CH3:6])([CH3:4])[CH2:2][C:9]12[CH:13]=[CH:14][CH:15]=[CH:16][CH:8]1[C:7]([NH:11][C:10]2=[O:12])=[O:17]

参加物

5

反応物 3

HCID 5238Sodium IodideHCID 684091-Chloro-2-methylpropan-2-olHCID 24194345Phthalimide potassium salt

生成物 1

HCID 685388332-(2-Hydroxyisobutyl)-Phthalimide収率 37%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 1-chloro-2-methyl-2-propanol (2.23 g, 97%, 0.02 mol), potassium phthalimide (3.780 g, 98%, 0.02 mol) and sodium iodide (60 mg, 4 mmol) in anhydrous DMF (40 mL) was heated to reflux overnight. The solvent was evaporated under reduced pressure. The resulting product was triturated with a mixture of 3:2 ethyl acetate/hexanes and the ensuing white precipitate was removed by filtration. The yellow filtrate was concentrated under reduced pressure and purified by flash chromatography in a mixture of 2:3 ethyl acetate/hexanes. The impure product thus isolated was triturated with hot hexanes (125 mL) and filtered to remove an insoluble white impurity. After evaporation of the solvent under reduced pressure, the obtained white solid was recrystallized in hexanes. The product was yielded as colorless crystals that were collected by filtration and dried under high vacuum (1.63 g, 37% yield). m.p.: 104-105° C.; TLC Rf 0.20 (2:3 ethyl acetate/hexanes); FTIR (KBr): 3524, 3456, 3097, 3031, 2973, 2930, 1773, 1698, 1611, 1466, 1427, 1389, 1319, 1190, 1076, 990, 965, 912, 890, 838, 766, 724, 712, 638 cm−1; 1H-NMR (500 MHz, CDCl3): δ 1.26 (s, 6H, 2 CH3), 2.74 (s, 1H, OH), 3.75 (s, 2H, CH2), 7.72 (dd, 2H, Jo=5.44 Hz, Jm=3.04 Hz, 2 Hc), 7.85 (dd, 2H, Jo=5.42 Hz, Jm=3.06 Hz, 2 Hh); 13C-NMR (126 MHz, CDCl3): δ 27.6 (2 CH3), 49.3 (CH2), 71.6 (CMe2), 123.6 (2 Cb), 132.0 (2 Ca), 134.3 (2 Cc), 169.3 (2 CO).

後処理

  1. temperatureto reflux overnight
  2. customThe solvent was evaporated under reduced pressure
  3. customThe resulting product was triturated with a mixture of 3:2 ethyl acetate/hexanes
  4. customthe ensuing white precipitate was removed by filtration
  5. concentrationThe yellow filtrate was concentrated under reduced pressure
  6. custompurified by flash chromatography in a mixture of 2:3 ethyl acetate/hexanes
  7. customThe impure product thus isolated
  8. customwas triturated with hot hexanes (125 mL)
  9. filtrationfiltered
  10. customto remove an insoluble white impurity
  11. customAfter evaporation of the solvent under reduced pressure
  12. customthe obtained white solid was recrystallized in hexanes
  13. customThe product was yielded as colorless crystals that
  14. filtrationwere collected by filtration
  15. customdried under high vacuum (1.63 g, 37% yield)

出典と根拠

ORDレコード
ord-e125606472b64c2c96bb003f4af077b8
出典データセット
uspto-grants-2014_04
特許番号
US08703987B2

関連ノート

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