Tributylphosphine → HCID 58629833, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of the 1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanol (50 mg, 0.16 mmol) and ethyl 3-(4-hydroxyphenyl)propanoate (31 mg, 0.16 mmol) in anhydrous THF (3.2 mL) under nitrogen at 0° C. (ice/water bath) was added ADDM (83 mg, 0.32 mmol). After a few minutes, nBu3P (81 μL, 0.32 mmol) was added (drop-wise) and the solution was stirred at 0° C. warming to rt overnight. After 17.5 hours the solvent was concentrated under vacuum and the solid residue dissolved in DCM (5 mL) and washed with water (5 mL) using a hydrophobic frit. The aqueous layer was re-extracted with DCM (5 mL) and the combined organic layers concentrated under vacuum. The resulting solid residue was then purified by SPE (silica, 5 g cartridge) eluting with cyclohexane:EtOAc (gradient 100:1 to 1:1) to afford the title compound (29 mg).

Provenance & Evidence