Potassium Hydroxide → 3-Methyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzaldehyde

Participants

Reaction Conditions

Reaction Steps

4-Hydroxy-3-methylbenzaldehyde (9 g, 66.10 mmol), methanesulfonic acid 2-(5-methyl-2-phenyl-oxazol-4-yl)-ethyl ester [PCT Int. Appl. (2000) WO0008002] (22.5 g, 80 mmol), KOH (80 mmol, 4.48 g) and tetrabutylammonium-hydrogensulfate (2 g) in 400 ml toluene/100 ml water were heated at 80° C. during 17 hours. The reaction mixture was then cooled to 0° C., washed with water/ice and brine, the aqueous layer extracted with tBuOMe, 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 CH2Cl2/heptane to yield 15 g (72%) of the title compound as a white solid.

Provenance & Evidence