Triphenylphosphine → HCID 17756287, compound

Participants

Reaction Steps

To a solution of 5-nitro-2-trifluoromethylphenol (2.83 g, 13.7 mmol), (R)-(+)-(tert-butoxy-carbonyl)-2-pyrrolidinemethanol (2.75 g, 13.7 mmol), and PPh3 (3.58 g, 13.7 mmol) in 24 mL THF, cooled at −20° C. was added dropwise over 1.5 h a 12 mL THF solution containing DEAD (2.43 g, 13.9 mmol). The mixture turned a deep red. The reaction was warmed gradually to RT and stirred for 18 h. The reaction was concentrated in vacuo and treated with a small mixture of hexanes and Et2O. After sonication, the solids were filtered off, and the filtrate was concentrated in vacuo. The crude was dissolved in a very small amount of EtOAc and Et2O then diluted with hexanes, which were washed once with 0.1N HCl, 3 times with 2N NaOH, and once with brine. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography using 5% EtOAc in hexanes to yield the title compound as a clear thick oil.

Provenance & Evidence