N-Hydroxyphthalimide → Ethyl 4-((1,3-dioxoisoindolin-2-yl)oxy)butanoate
Reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[OH:10][N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21].CCN(C(C)C)C(C)C.[Cl-].[NH4+]>CN(C)C=O>[CH2:8]([O:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2][O:10][N:11]1[C:15](=[O:16])[C:14]2[C:13](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]1=[O:21])[CH3:9]Participants
Conditions
- Temperature
- 80 °C
Procedure
To a solution of ethyl 4-bromo-n-butyrate (1.2 g, 6.13 mmol) in dimethylformamide (9 ml), N-hydroxyphthalimide (1.5 g, 9.19 mmol) and Hunig base (N,N-diisopropylethylamine, 2.13 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 4-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-butyric acid ethyl ester (1.47 g, 100%).
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-f08372e9a4b044d1b58943409e85c085
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08084645B2
Reaction notes
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