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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1022842Generated: November 3, 2026

1-Butanol → HCID 67124168, compound

https://huagongshe.com/reaction/1022842

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-ButanolHCID 263—
ReactantDicyclohexylamineHCID 7582—
ReactantHCID 22660526HCID 22660526—
Reactant3-(4-Bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazoleHCID 23159812—
CatalystPalladiumHCID 23938—
Catalyst1,3-Bis(diphenylphosphino)propaneHCID 81219—
SolventAcetic AcidHCID 176—
SolventEthyl AcetateHCID 8857—
ProductHCID 67124168HCID 6712416860%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08722673B2
Source datasetuspto-grants-2014_05
ORD IDord-aecc61fcc4724afca3f05c1983d8109f
Source noteuspto-grants-2014_05