HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → HCID 67124168, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | alpha-Cyclohexylcyclohexanemethanamine | HCID 10774245 | — |
| 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 | 1-Butanol | HCID 263 | — |
| 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), 1,3-bis(diphenylphosphine)propane (dppp, 9 mg), palladium on charcoal (10%, 23 mg), dicylohexylmethylamine (259 mg) and n-butanol (3 mL) were stirred under an atmosphere of nitrogen at reflux over night. After cooling, ethyl acetate (30 mL) and aqueous hydrochloric acid (1 M, 20 mL) were added and the mixture was stirred at room temperature for 1 h. After filtration, the layers were separated, the organic layer was extracted with 1 M HCl, dried (Na2SO4) and evaporated in vacuum. Purification of the residue on silica gel afforded the title compound (270 mg, 60%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08999889B2 |
| Source dataset | uspto-grants-2015_04 |
| ORD ID | ord-1a714dd0f8c34c219a5d67336a747b1b |
| Source note | uspto-grants-2015_04 |