Potassium Hydroxide → 2-(4-Methoxy-benzyloxy)-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzaldehyde

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-hydroxy-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzaldehyde (54 mg, 0.167 mmol), 4-methoxy-benzylchloride (58 mg, 0.368 mmol), KOH (56 mg, 1 mmol) and tetrabutylammonium-hydrogensulfate (50 mg) in 6 ml toluene and 5 ml water was heated at 80° C. during 6 hours. The reaction mixture was then cooled to 0° C., washed with water/ice and brine, the aqueous layer extracted with AcOEt, the combined organic layers dried over Na2SO4 and evaporated. The crude product was purified by chromatography (SiO2; AcOEt/heptane) and the product was crystallized from heptane to yield 25 mg (34%) as a white solid.

Provenance & Evidence