2-(Chloroethoxy)ethanol → 2-(2-(2-Hydroxyethoxy)ethyl)-1H-isoindole-1,3(2H)-dione
Reaction equation
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]12Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
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.