Potassium Iodide → [Rac]-3-[4-(2-tert-butyl-5-methyl-oxazol-4-ylmethoxy)-2-methyl-phenyl]-2-ethoxy-propionic acid ethyl ester

Participants

Reaction Steps

A mixture of [rac]-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid ethyl ester (50 mg, 0.2 mmol), 2-tert-butyl-4-chloromethyl-5-methyl-oxazole (41 mg, 0.22 mmol, example 1, step b]), cesium carbonate (71 mg, 0.22 mmol) and a trace of potassium iodide were suspended in acetone (5 ml). The suspension was heated under reflux for 14 h, the solvent evaporated under reduced pressure and the residue dissolved in 2 N HCl/ice water 1/1 and ethyl acetate. The layers were separated and the aqueous layer was extracted two times with ethyl acetate. The combined organic layers were washed two times with brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography (silica gel, cyclohexane/AcOEt) to give 50 mg (0.12 mmol, 63%) of the title compound as colorless oil.

Provenance & Evidence