Sulfuric Acid → 2-{2-Methoxymethyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenoxy)-2-methylpropionic acid ethyl ester

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Reaction Steps

A 15 mL round bottomed flask under a nitrogen atmosphere were charged with 2-{2-hydroxymethyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenoxy}-2-methylpropionic acid ethyl ester (0.075 g, 0.17 mmol), anhydrous DMF (1 mL), and then methyl iodide (0.16 mL, 1.7 mmol). The solution was cooled in an ice bath and was treated with NaH (0.014 g, 0.34 mmol, 60% oil dispersion). The mixture was stirred for 2 h, poured into EtOAc (6 mL) and brine (10 mL), and acidified using dilute sulfuric acid. The organic layer was separated, dried (Na2SO4), and concentrated to an oil. The crude product was purified using radial chromatography (EtOAc:Hex 15:85) to give a colorless oil (0.039 g, 51%). MS (ES) m/e 454 (M+1).

Provenance & Evidence