Sodium hydride → Dimethyl 5-(2-oxopyrrolidin-1-yl)isophthalate
Reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:9]=[C:10]([C:18]([O:20][CH3:21])=[O:19])[CH:11]=[C:12]([CH:17]=1)[C:13]([O:15][CH3:16])=[O:14])=[O:6].[H-].[Na+]>CN(C=O)C>[O:6]=[C:5]1[CH2:4][CH2:3][CH2:2][N:7]1[C:8]1[CH:9]=[C:10]([C:18]([O:20][CH3:21])=[O:19])[CH:11]=[C:12]([CH:17]=1)[C:13]([O:15][CH3:16])=[O:14]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A solution of dimethyl 5-(4-chlorobutanamido)isophthalate (0.635 g, 2.02 mmol, 1 eq) dissolved in 5 ml anhydrous DMF was added dropwise to a stirred suspension of NaH (60% dispersion in oil, 0.101 g, 2.53 mmol, 1.25 eq) in 2 ml anhydrous DMF at 0° C. under Ar. The reaction was stirred at 0° C. to room temperature overnight. After stirring overnight the reaction was heated to 100° C. for 19 h. After cooling to room temperature the reaction was poured into ice-water to quench. The mixture was extracted with EtOAc (×1). The organic layer was washed with water (×4), brine (×1), and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo. Purification via flash chromatography yielded 0.3487 g (1.26 mmol, 62% yield) of the product.
Workup
- stirringAfter stirring overnight the reaction
- temperatureAfter cooling to room temperature the reaction
- customto quench
- extractionThe mixture was extracted with EtOAc (×1)
- washThe organic layer was washed with water (×4), brine (×1)
- dry with materialdried over Na2SO4
- filtrationThe inorganics were filtered off
- customthe solvent was removed in vacuo
- customPurification via flash chromatography
Sources & evidence
- ORD record
- ord-193624aeb5484aa086e50ecdb11b1192
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299267B2
Reaction notes
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