Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2-(3,3,3-Trifluoro-2-hydroxy-2-methylpropyl)-1H-isoindole-1,3(2H)-dione | HCID 67383644 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67383555 | HCID 67383555 | — |
Reaction Steps
To a stirring solution of 2-(3,3,3-trifluoro-2-hydroxy-2-methylpropyl)isoindoline-1,3-dione (250 mg, 0.915 mmol)) at 0° C. in THF (8 ml), NaH (80 mg, 2 mmol) was added. After 30 minutes methyl iodide (1.299, 9.15 mmol) was added. The reaction mixture was left stirring in a ice-bath and allowed to warm to 25° C. over 3.5 hours. The reaction was quenched with sat. NH4Cl and the mixture extracted with DCM. The organic extract was separated using a phase separator and purification by chromatography on silica, eluting in a 0% to 30% iso-hexane:EtOAc afforded the title product; 1H NMR (400 MHz, Methanol-d4) δ 7.91 (2H, m), 7.85 (2H, m), 3.97 (2H, m), 3.44 (3H, s), 1.42 (3H, s);
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08476269B2 |
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| Source dataset | uspto-grants-2013_07 |
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| ORD ID | ord-fba7ab7898364fe7a043d6cd1a79e490 |
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| Source note | uspto-grants-2013_07 |
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