Dimethylformamide → HCID 68887611, compound

Participants

Reaction Steps

A mixture of 4-(2-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (0.98 g), methyl 2-(4-hydroxyphenyl)acetate (0.51 g), anhydrous potassium carbonate (0.52 g), and N,N-dimethylformamide (10 mL) was stirred at room temperature for 3 hrs. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with dilute hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was subjected to silica gel column chromatography to give an oil from a fraction eluted with ethyl acetate-hexane (1:4, v/v). To a mixture of the obtained oil, tetrahydrofuran (6 mL), and methanol (6 mL) was added a 1N aqueous sodium hydroxide solution (6 mL) and the mixture was stirred at room temperature for 2 hrs. Dilute hydrochloric acid was added to acidify the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give crystals (1.00 g, 76%) of 2-[4-[2-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetic acid. Recrystallization from acetone-hexane gave colorless prism crystals. melting point: 173-174° C.

Provenance & Evidence