Acetone → [4-(5-Acetyl-6-hydroxy-biphenyl-2-yloxymethyl)-phenyl]-(hydroxy-methyl]-benzonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(2,6-dihydroxy-biphenyl-3-yl)-ethanone (446 mg, 1.95 mmol) and 3-[(4-iodomethyl-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile (848 mg, 1.95 mmol) in acetone (50 mL) is added potassium carbonate (450 mg, 3.25 mmol). The suspension is heated at 50° C. for 14 hours. After cooling to room temperature, the mixture is poured onto saturated ammonium chloride (15 mL) and extracted with ethyl acetate (4×20 mL). The combined organic extracts are combined; washed with brine; dried over magnesium sulfate; filtered and concentrated under reduced pressure to a light-yellow oil: MS (m/z): 523 (M+). The residue is then dissolved in methanol and p-toluenesulfonic acid monohydrate is added. After 1 hour, the solvent is removed under reduced pressure. The resulting residue is purified by flash chromatography (20% to 45% ethyl acetate/hexanes) to give the title compound as a foam: MS (m/z): 449 (M+), 432 (M−OH).

Provenance & Evidence