Triphenylphosphine → 4-{3-[2-(4-Methoxy-phenyl)-5-methyl-oxazol-4-yl]-propoxy}-naphthalene-1-carbaldehyde

Participants

Reaction Steps

g of the above prepared 3-[2-(4-methoxy-phenyl)-5-methyl-oxazol-4-yl]-propan-1ol (4.04 mmol) was dissolved in 21 ml of toluene and treated successively at 0° C. with 0.696 g of 4-hydroxy-naphthalene-1-carbaldehyde (4.04 mmol), 1.061 g of triphenylphosphine (4.04 mmol), and 0.818 g (4.04 mmol) of DIAD. The cooling bath was then removed and stirring continued for 3 h. Pouring onto crashed ice, twofold extraction with AcOEt, washing with 3N NaOH and water, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (silica gel, hexane/AcOEt=7/3) left finally 1.084 g of the title compound as light yellow gum.

Provenance & Evidence