Ethyl bromoacetate → Ethyl N-phthalimidoxyacetate
Reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[OH:8][N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19].CCN(C(C)C)C(C)C.[Cl-].[NH4+]>CN(C)C=O>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][O:8][N:9]1[C:13](=[O:14])[C:12]2[C:11](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]1=[O:19])[CH3:7]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of ethyl bromoacetate (2.05 g, 12.3 mmol) in dimethylformamide (15 ml), N-hydroxyphthalimide (3.04 g, 18.4 mmol) and Hunig base (N,N-diisopropylethylamine, 4.24 mL) were added at room temperature, and the mixture was stirred at 80° C. overnight. The reaction solution was poured into saturated aqueous solution of ammonium chloride, and the resulting mixture was extracted with ethyl acetate (3×40 ml). The combined organic layer was washed with saturated brine (2×30 ml), dried over Na2SO4, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (100 g, n-hexane/ethyl acetate=2:1) to give (1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-acetic acid ethyl ester (1.83 g, 60%) as a pale yellow solid.
Workup
- extractionthe resulting mixture was extracted with ethyl acetate (3×40 ml)
- washThe combined organic layer was washed with saturated brine (2×30 ml)
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography (100 g, n-hexane/ethyl acetate=2:1)
Sources & evidence
- ORD record
- ord-26b9b49b727149b3941ba8551007c482
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08084645B2
Reaction notes
Loading…