Tetrahydrofuran → [4-({4-[(5-Methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenoxy}methyl)-2-phenyl-1,3-oxazol-5-yl]methanol

Participants

Reaction Steps

To a mixture of 5-(tert-butyldiphenylsilyloxymethyl)-4-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenoxy]methyl]-2-phenyl-1,3-oxazole (1.44 g) and tetrahydrofuran (30 mL) was added tetrabutylammonium fluoride (1M tetrahydrofuran solution, 5 mL) at 0° C., and the mixture was stirred at room temperature for 30 min. Water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give [4-({4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenoxy}methyl)-2-phenyl-1,3-oxazol-5-yl]methanol as colorless crystals (0.55 g, yield 59%) from a fraction eluted with ethyl acetate-hexane (2:1, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 157-158° C.

Provenance & Evidence