1,4-Dioxane → HCID 22221246, compound

Participants

Reaction Steps

A mixture of 3-[5-(4-bromophenyl)-4-isoxazolyl]propan-1-ol (1.10 g), copper cyanide (1.41 g), tris(dibenzylideneacetone)dipalladium (130 mg), 1,1′-bis(diphenylphosphino)ferrocene (314 mg), tetraethylammonium cyanide (553 mg) and 1,4-dioxane (20 ml) was refluxed for 3.5 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and 3-[5-(4-cyanophenyl)-4-isoxazolyl]propan-1-ol (418 mg, yield 52%) was obtained as pale yellow crystals from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point: 82–83° C.

Provenance & Evidence