N-Hydroxyphthalimide → 2-(3-Methylbut-2-enyloxy)isoindoline-1,3-dione
Reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].Br[CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17].[OH-].[K+]>C(O)C>[CH3:17][C:16]([CH3:18])=[CH:15][CH2:14][O:1][N:2]1[C:3](=[O:12])[C:4]2[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:7]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a stirring solution of N-hydroxyphthalimide (Aldrich, 1.63 g, 10.0 mmol) in anhydrous ethanol (50 mL) was added 1-bromo-3-methyl-but-2-ene (Aldrich, 1.4 mL, 12.0 mmol) and potassium hydroxide (0.67 g, 12.0 mmol). After the reaction was allowed to stir at 50° C. for 4 hours, it was concentrated in vacuo and then dissolved in ethyl acetate and partitioned with water. The organic layer was washed twice with water, twice with saturated sodium chloride solution, collected and dried over Na2SO4, filtered and concentrated in vacuo, affording a white solid. The collected solid was purified via silica column in 10% methanol in dichloromethane to afford 2-(3-methyl-but-2-enyloxy)-isoindole-1,3-dione (0.53 g, 23%): 1H NMR (400 MHz; DMSO-d6) δ 7.81 (s, 4H), 5.38 (t, 1H, J=1.5), 4.57 (d, 2H, J=7.6). 1.67 (s, 3H), 1.62 (s, 3H); MS (APCI+)=232.0.
Workup
- concentrationit was concentrated in vacuo
- dissolutiondissolved in ethyl acetate
- custompartitioned with water
- washThe organic layer was washed twice with water, twice with saturated sodium chloride solution
- customcollected
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customaffording a white solid
- customThe collected solid was purified via silica column in 10% methanol in dichloromethane
Sources & evidence
- ORD record
- ord-7c14d1510c9f488e90b211307ee1cc19
- Source dataset
- uspto-grants-2008_08
- Patent number
- US07411001B2
Reaction notes
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