Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Diisobutylaluminumhydride | HCID 21225700 | — |
| Reactant | HCID 68409423 | HCID 68409423 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 68410437 | HCID 68410437 | 96% |
Reaction Steps
A solution of ethyl 1-phenyl-5-[(phenylsulfonyl)amino]-1H-pyrazole-3-carboxylate (445 mg) in tetrahydrofuran (10 mL) was cooled to −78° C., and a 1.5 mol/L solution (4 mL) of diisobutylaluminum hydride in toluene was added dropwise. After stirring at 0° C. for 1 hr, the mixture was treated with 1 mol/L hydrochloric acid, and extracted with ethyl acetate. The aqueous layer was extracted with ethyl acetate again, and the combined extracts were washed with 1.0 mol/L hydrochloric acid, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=1:1→1:3) to give the title compound as a pale-yellow oil (yield 379 mg, yield 96%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08334301B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-f511556fece247c8a7082fba2335d78d |
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| Source note | uspto-grants-2012_12 |
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