HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → ethyl 1-({5-methyl-4-[3-(trifluoromethyl)phenyl]furan-2-yl}methyl)-1H-pyrazole-4-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Diisopropyl diazene-1,2-dicarboxylate | HCID 75555 | — |
| Reactant | ethyl 1H-pyrazole-4-carboxylate | HCID 142179 | — |
| Reactant | {5-Methyl-4-[3-(trifluoromethyl)phenyl]furan-2-yl}methanol | HCID 66939730 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | ethyl 1-({5-methyl-4-[3-(trifluoromethyl)phenyl]furan-2-yl}methyl)-1H-pyrazole-4-carboxylate | HCID 66939161 | 33.9% |
Reaction Steps
A solution of the compound (0.40 g) obtained in Example 128d, ethyl 1H-pyrazole-4-carboxylate (0.26 g) and triphenylphosphine (0.49 g) in tetrahydrofuran (5 mL) was cooled in an ice bath, diisopropyl azodicarboxylate (0.36 mL) was added, and the mixture was stirred at the same temperature for 1 hr. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane/ethyl acetate) to give the title compound (0.20 g) as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08461348B2 |
| Source dataset | uspto-grants-2013_06 |
| ORD ID | ord-5d7162b648d94ffdbf2c2139c9857ea8 |
| Source note | uspto-grants-2013_06 |