Triphenylphosphine → HCID 69034312, compound

Participants

Reaction Conditions

Reaction Steps

3-Hydroxy-5-nitrobenzotrifluoride (5 g, 24.1 mmol, 1 eq), (S)-3-hydroxytetrahydrofuran (1.9 mL, 24.1 mmol, 1 eq), PPh3 (6.3 g, 24.1 mmol, 1 eq) were dissolved in 43 mL of THF. The solution was cooled to −20° C. DIAD (4.8 mL, 24.6 mmol, 1.02 eq) was added in 22 mL of THF over the course of 2 h while the temperature was maintained between −10 and −20° C. After the addition was complete the reaction was stirred for 3 days at RT. The solvent was removed in vacuo. The residue was stirred with ˜250 mL of hexane for 45 min during which time triphenylphosphine oxide precipitated as a white solid. The solid was removed by filtration and the filtrate was washed twice with 2 N NaOH and once with brine. After drying over Na2SO4 the solution was filtered and the solvent removed under reduced pressure. The crude material was purified by chromatography on a Biotage system eluting with a gradient of 5 to 15% EtOAc:hexane to yield the desired compound.

Provenance & Evidence