Nitroethane → HCID 178435547, compound

Participants

Reaction Steps

A 40 mL vial equipped with a magnetic stir bar was charged with 2-bromo-6-(trans-4-tert-butylcyclohexyloxy)naphthalene (0.6695 g, 1.853 mmol), tris(dibenzylideneacetone)dipalladium(O) (0.06363 g, 0.06948 mmol), 2-(di-t-butylphosphino)-2′-methylbiphenyl (0.08684 g, 0.2779 mmol), and cesium carbonate (0.7245 g, 2.224 mmol). The reaction vessel was capped, evacuated, and backfilled with argon three times then 1,2-dimethoxyethane (20.00 mL, 192.4 mmol) was added via syringe under argon. After the mixture was stirred vigorously for 2 min at room temperature, nitroethane (0.2795 mL, 3.891 mmol) was added and the reaction was heated overnight at 50° C. The reaction was allowed to cool to ambient temperature. The mixture was quenched with a solution of sat. aqueous ammonium chloride. The layers were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phase was washed with water then dried with magnesium sulfate, filtered and concentrated under reduced pressure. The residue was taken up in methylene chloride and silica gel was added. The solvent was removed and the residue was purified by flash column chromatography using 0-20% ethylacetate in hexanes to give the title compound in 58% yield.

Provenance & Evidence