Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 12149023 | HCID 12149023 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 12149030 | HCID 12149030 | — |
Reaction Steps
Under argon atmosphere, 60% sodium hydride (30 mg) was added at 0° C. to a solution of Compound 1 (253.8 mg) in tetrahydrofuran (5 mL), and the mixture was stirred for 30 minutes at room temperature. Under cooling with ice, methyl iodide (0.16 mL) was added thereto, and the resultant mixture was stirred for 88 hours at room temperature. Water was added to the reaction mixture, and the solvent was distilled off. The residue was subjected to extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the resultant crude product was subjected to purification through silica gel column chromatography (ethyl acetate-hexane=1:4 to 1:2), to thereby yield 139.3 mg of the title compound as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06933309B2 |
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| Source dataset | uspto-grants-2005_08 |
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| ORD ID | ord-0503f4689a8a47b5b098de86eedccd92 |
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| Source note | uspto-grants-2005_08 |
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