Triphenylphosphine Oxide → 2-(1-{4-[1-(4-Iodophenyl)-1,2-dimethylpropyl]phenoxy}-1-methylethyl)pyridine

Participants

Reaction Steps

A solution of triflic anhydride (1 equiv.) in DCM is added to a solution of triphenylphosphine oxide (2 equiv) in DCM at 0° C. After precipitation is observed (˜15 min), a solution of 5e (1 equiv) in DCM is added. After 5 min, sodium borohydride (4 equiv.) is added in one portion. After completion of reaction, the reaction mixture is quenched with 2 N HCl, poured into saturated aqueous sodium bicarbonate and extracted three times with EtOAc. The combined organic extracts are washed with water, brine, dried (Na2SO4) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel affords the title compound 5f.

Provenance & Evidence