Toluene → HCID 23076344, compound

Participants

Reaction Steps

To a mixture of methyl 2-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-5-hydroxymethylbenzoate (2.50 g) and toluene (100 mL) was added thionyl chloride (0.95 g), and the mixture was heated under reflux for 1 hr. After concentration of the reaction mixture, ethyl acetate was added to the residue, and the mixture was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated to give methyl 5-chloromethyl-2-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}benzoate as colorless crystals (2.23 g, yield 84%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 107-108° C.

Provenance & Evidence