HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Butanol → HCID 67124168, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Butanol | HCID 263 | — |
| Reactant | Dicyclohexylamine | HCID 7582 | — |
| Reactant | HCID 22660526 | HCID 22660526 | — |
| Reactant | 3-(4-Bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole | HCID 23159812 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Catalyst | 1,3-Bis(diphenylphosphino)propane | HCID 81219 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67124168 | HCID 67124168 | 60% |
Reaction Steps
A mixture of 3-(4-bromo-3-methyl-phenyl)-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole (500 mg), 1,4-butandiol-monovinyl-ether (385 mg), palladium on charcoal (10%, 23 mg), 1,3-bis(diphenylphosphino)propane (9 mg), dicyclohexylamine (259 mg) and n-butanol (3 mL) were refluxed over night. Ethyl acetate (30 mL) and aqueous acetic acid (1 M, 20 mL) were added, and left at room temperature for 1 h. After separation of the layers, the organic layer was washed with HCl (1 M, 10 mL), dried (Na2SO4) and concentrated in vacuum. The residue was purified by flash chromatography on silica gel to yield the title compound (270 mg, 60%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08722673B2 |
| Source dataset | uspto-grants-2014_05 |
| ORD ID | ord-aecc61fcc4724afca3f05c1983d8109f |
| Source note | uspto-grants-2014_05 |