Cyclohexyl methyl ketone → HCID 58495622, compound

Participants

Reaction Conditions

Reaction Steps

Add 4-iodobenzonitrile (1.0 g, 4.37 mmol) and 1-cyclohexyl-ethanone (717 mg, 5.68 mmol) to a suspension of tris(dibenzylideneacetone)dipalladium(0) (60 mg, 0.065 mmol), BINAP (98 mg, 0.157 mmol) and sodium tert-butoxide (546 mg, 5.68 mmol) in anhydrous THF (26 mL). Heat the mixture at 70° C. under nitrogen atmosphere. After 6 h, add tris(dibenzylideneacetone)dipalladium(0) (60 mg, 0.065 mmol), BINAP (98 mg, 0.157 mmol), sodium tert-butoxide (294 mg, 3.06 mmol) and 1-cyclohexyl-ethanone (386 mg, 3.06 mmol) and allow to stir the mixture at 70° C. under nitrogen overnight. Add water and extract twice with EtOAc. Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (92:8) to obtain the desired intermediate as a yellow oil (902 mg, 91%).

Provenance & Evidence