Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | HCID 66682498 | HCID 66682498 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 66682505 | HCID 66682505 | 91% |
Reaction Steps
5-Methyl-2-[1-(triisopropylsilyl)-1H-pyrrol-2-yl]-1,3-thiazole (215 mg, 0.67 mmol) synthesized in Example (3b) was dissolved in tetrahydrofuran (8 mL), and tetrabutylammonium fluoride (1M tetrahydrofuran solution, 0.87 mL, 0.87 mmol) was added, followed by stirring at room temperature for 30 minutes under nitrogen atmosphere. Water (10 mL) was added, and extraction was carried out with diethyl ether (20 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=5%-30%) to afford the desired compound (100 mg, yield 91%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08415359B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-f09a933e83294b809782cbe0e46a8207 |
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| Source note | uspto-grants-2013_04 |
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