Tributylphosphine → Ethyl {[2-methyl-4-({1-[4'-(trifluoromethyl)-4-biphenylyl]pentyl}oxy)phenyl]oxy}acetate

Participants

Reaction Steps

To a solution of 1-[4′-(trifluoromethyl)-4-biphenylyl]-1-pentanol (250 mg, 0.81 mmol) in dry THF (20 mL) under nitrogen at 0° C. (ice/water bath) was added nBu3P (0.41 mL, 1.64 mmol), followed by ethyl (4-hydroxy-2-methylphenoxy)acetate (170 mg, 0.81 mmol) and ADDM (420 mg, 1.64 mmol) portion-wise. After stirring the mixture for 18 hours at rt under nitrogen the solvent was removed under vacuum. The residue was partitioned between water and EtOAc and the aqueous re-extracted with EtOAc (3×30 mL). The organic combined extract was dried (MgSO4) and then reduced under vacuum. Purification by flash chromatography (silica), eluting with cyclohexane:EtOAc (9:1) afforded the title compound as a colourless gum (310 mg).

Provenance & Evidence