Tributylphosphine → Ethyl ({2-methyl-4-[(1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}hexyl)oxy]phenyl}oxy)acetate

Participants

Reaction Steps

A solution of 1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}-1-hexanol (131 mg, 0.41 mmol) in dry THF (15 mL) under nitrogen was cooled to 0° C. and treated with ethyl (4-hydroxy-2-methylphenoxy)acetate (85 mg, 0.41 mmol), ADDM (210 mg, 0.82 mmol) and nBu3P (204 μL, 0.82 mmol). The reaction mixture was then allowed to warm to rt slowly over 22 hours. The solvent was removed under vacuum and the residue partitioned between EtOAc (2×30 mL) and water (30 mL). The layers were separated and the organic layer dried (Na2SO4) and reduced. Purification by SPE (silica, 20 g cartridge) eluting with cyclohexane:EtOAc (49:1 to 24:1) afforded the title compound as a colourless oil (80 mg).

Provenance & Evidence