Tributylphosphine → Ethyl ({2-methyl-4-[(3-methyl-1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}butyl)oxy]phenyl}oxy)acetate

Participants

Reaction Conditions

Reaction Steps

A solution of 3-methyl-1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}-1-butanol (180 mg, 0.58 mmol) in dry THF (12 mL) under nitrogen was treated with ethyl (4-hydroxy-2-methylphenoxy)acetate (122 mg, 0.58 mmol) and cooled to 0° C. This was treated portion-wise with ADDP (0.3 g, 1.2 mmol), then drop-wise with nBu3P (0.29 mL, 1.2 mmol). The resulting pale yellow suspension allowed to warm to rt slowly over 16 hours. The solvent was removed under vacuum and the residue partitioned between EtOAc (60 mL) and water (60 mL) and the layers separated. The aqueous was re-extracted with EtOAc (60 mL) and the combined organic layer dried (Na2SO4) and reduced. Purification by SPE (silica, 10 g cartridge) eluting with cyclohexane:EtOAc (gradient 99:1 to 49:1) gave the title compound as a colourless oil (137 mg).

Provenance & Evidence