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

Participants

Reaction Steps

To a 15 mL round bottom flask under a nitrogen atmosphere were charged 0.075 g (0.17 mmol) of 2-{2-hydroxymethyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenoxy}-2-methylpropionic acid ethyl ester, dissolved in 1 mL of anhydrous DMF, followed by the addition of 0.16 mL (1.7 mmol) of methyl iodide. The reaction solution was cooled down in an ice bath and was treated with 0.014 g (0.34 mmol) of NaH. The reaction was stirred cold for 2 h. Next the reaction was poured into 6 mL of EtOAc and 10 mL of brine, and then acidified using dilute sulfuric acid. The organic layer was separated away, dried over Na2SO4, and removed in vacuo to give a crude oil. This crude residue was purified using radial chromatography with a 1 mm normal phase silica gel plate, eluting with 15:85 EtOAc:Hex to give a colorless oil (0.039 g, 51%). MS (ES) m/e 454 (M+1).

Provenance & Evidence