Hydrogen iodide → HCID 15020365, compound

Participants

Reaction Steps

A mixture of α-cyclohexyl-α-(4-fluorophenyl)-4-pyridinemethanol (16.54 g, 0.058 mole), 57% hydrogen iodide (250 ml), glacial acetic acid (250 ml), and phosphorus (50.0 g) was heated overnight at reflux. The reaction mixture was cooled and filtered through Celite®. The volume of the filtrate was concentrated to 100 ml. Ice/50% sodium hydroxide was added, and the aqueous phase was extracted with chloroform. The chloroform layer was back extracted with 5% sodium hydroxide and water. The organic layer was dried over sodium sulfate and filtered, and solvent removed to give a green oil. A 4 g portion of this oil was subjected to flash chromatography on silica gel using 20% ethyl acetate-hexanes for elution. Fractions of similar purity were combined and solvent removed to give an oil. This oil was dried in vacuo overnight at 80° C. The oil crystallized to give 2.95 g (19% yield) of white, crystalline solid, mp 78°-81° C.

Provenance & Evidence