2-(Chloroethoxy)ethanol → 2-(2-(2-Hydroxyethoxy)ethyl)-1H-isoindole-1,3(2H)-dione

HRID 399579

反応式

HRID 399579 の反応式
Cl[CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7].[C:8]1(=[O:18])[NH:12][C:11](=[O:13])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]12.[K]>CN(C)C=O>[C:8]1(=[O:18])[N:12]([CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7])[C:11](=[O:13])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]12

参加物

4

反応物 2

HCID 123612-(Chloroethoxy)ethanolHCID 24194345Phthalimide potassium salt

生成物 1

HCID 27554062-(2-(2-Hydroxyethoxy)ethyl)-1H-isoindole-1,3(2H)-dione収率 64.17%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

To a solution of 2-(2-chloroethoxy)ethanol 14 (5 mL, 47.4 mmol) in N,N-dimethylformamide (35 mL) was added potassium phthalimide 2 (8.8 g, 47.51 mmol), and the reaction mixture was stirred for 20 h at 70° C. The mixture was concentrated and then diluted with dichloromethane (300 mL), and the organic layer was washed with water, dried, and concentrated. The residue was purified by flash column chromatography (3:2 to 2:3 hexane-ethyl acetate) to give compound 15 as a white solid (7.15 g, 64.17%) having an RF of 0.12 (solvent 3:2 hexane-ethyl acetate). See FIG. 9.

後処理

  1. concentrationThe mixture was concentrated
  2. additiondiluted with dichloromethane (300 mL)
  3. washthe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (3:2 to 2:3 hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-cf405ceb7bdf43ffb257a0be49cbc372
出典データセット
uspto-grants-1998_10
特許番号
US05821356

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