N-Iodosuccinimide → (4-Iodo-3-methylisoxazol-5-yl)acetic acid methyl ester
Reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[O:4][N:3]=1.[I:12]N1C(=O)CCC1=O>FC(F)(F)C(O)=O>[I:12][C:6]1[C:2]([CH3:1])=[N:3][O:4][C:5]=1[CH2:7][C:8]([O:10][CH3:11])=[O:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
To a sealed tube fitted with magnetic stirrer was charged methyl (3-methyl-1,2-oxazol-5-yl)acetate (0.9 g, 5.8 mmol) and N-iodosuccinimide (2.61 g, 11.6 mmol) in 10 mL trifluoroacetic acid. The reaction mixture was heated at 65° C. for 3 h. The RM was quenched with NaHCO3 solution (25 mL) and extracted with ethyl acetate (30 mL). The organic layer was washed with water (30 mL) and saturated brine solution (30 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as brown solid (1.18 g, yield: 72.4%).
Workup
- customTo a sealed tube fitted with magnetic stirrer
- customThe RM was quenched with NaHCO3 solution (25 mL)
- extractionextracted with ethyl acetate (30 mL)
- washThe organic layer was washed with water (30 mL) and saturated brine solution (30 mL)
- dry with materialThe organic layer was dried over anhydrous Na2SO4
- customthe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-b802d6b9b7f54f6ba2613b59b6818ddd
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09278915B2
Reaction notes
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