Tributylphosphine → Ethyl [(4-{[1-(6-bromo-2-pyridinyl)pentyl]oxy}-2-ethylphenyl)oxy]acetate

Participants

Reaction Steps

To a stirred solution of 1-(6-bromo-2-pyridinyl)-1-pentanol (250 mg, 1.02 mmol) and ethyl (4-hydroxy-2-ethylphenoxy)acetate (230 mg, 1.02 mmol) in dry THF (21 mL) at 0° C. (ice/water bath) under nitrogen was added ADDP (517 mg, 2.04 mmol) followed by nBu3P (510 μL, 2.04 mmol) drop-wise. The mixture was stirred with slow warming to rt over 18 hours and then concentrated under vacuum, diluted with EtOAc (150 mL) and washed with water (3×75 mL), dried (MgSO4), filtered and reduced to give an oil. Purification by SPE (silica, 10 g Cartridge) eluting with cyclohexane:EtOAc (gradient 20:1 to 5:1) afforded the title compound (307 mg).

Provenance & Evidence