Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Sodium Sulfate | HCID 24436 | — |
| Reactant | Diisobutylaluminumhydride | HCID 21225700 | — |
| Reactant | methyl 5-(trifluoromethoxy)-1H-indazole-3-carboxylate | HCID 45588292 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 178520041 | HCID 178520041 | 40.3% |
Reaction Steps
A solution of methyl 5-(trifluoromethoxy)-1H-indazole-3-carboxylate (0.370 g, 1.42 mmol) in THF (10 mL) was cooled to −10° C., and added dropwise with a 1 M solution of diisobutylaluminum hydride in toluene (5.11 mL, 5.11 mmol) over 5 minutes. The reaction mixture was stirred at −10° C. for 1 hour, and then stirred overnight at room temperature. The reaction mixture was added dropwise with saturated aqueous sodium sulfate under ice cooling to terminate the reaction, and then filtered through Celite. The filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol) to obtain the objective [5-(trifluoromethoxy)-1H-indazol-3-yl]methanol (0.133 g, 40%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09156827B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-874533de0c984c8495edb7e23cabd2be |
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| Source note | uspto-grants-2015_10 |
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