Phthalimide potassium salt → 2-[2-(4-Chloro-phenyl)-2-hydroxy-2-(4-iodo-phenyl)-ethyl]-isoindole-1,3-dione

HRID 45557

反応式

HRID 45557 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]3[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=3)[CH2:10][O:9]2)=[CH:4][CH:3]=1.[C:18]1(=[O:28])[NH:22][C:21](=[O:23])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12.[K]>C1COCC1.CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:9])([C:11]2[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=2)[CH2:10][N:22]2[C:18](=[O:28])[C:19]3[C:20](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:21]2=[O:23])=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 24194345Phthalimide potassium saltHCID 593172172-(4-Chlorophenyl)-2-(4-iodophenyl)oxirane

生成物 1

HCID 593319692-[2-(4-Chloro-phenyl)-2-hydroxy-2-(4-iodo-phenyl)-ethyl]-isoindole-1,3-dione収率 34%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2-(4-chloro-phenyl)-2-(4-iodo-phenyl)-oxirane* (571 mg, 1.60 mmol) and potassium phthalimide (340 mg, 1.84 mmol) in THF (5 mL) and DMSO (2 mL) was heated at 100° C. for 20 hours. The mixture was concentrated in vacuo, diluted with ethyl acetate and washed with water and brine (×2), dried (MgSO4), filtered and concentrated to give a crude product which was purified by column chromatography (SiO2), eluting with a gradient of ethyl acetate/petrol (2.5% to 100%) then 10% methanol/dichloromethane to give the title compound (273 mg, 34%); LCMS (PS-A2) Rt 3.22 min [M+H]+ 504.

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. additiondiluted with ethyl acetate
  3. washwashed with water and brine (×2)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude product which
  8. customwas purified by column chromatography (SiO2)
  9. washeluting with a gradient of ethyl acetate/petrol (2.5% to 100%)

出典と根拠

ORDレコード
ord-127b327b984c4858890977b1a36ff6a0
出典データセット
uspto-grants-2013_09
特許番号
US08541461B2

関連ノート

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