Tributylphosphine → Methyl 5-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]nicotinate

Participants

Reaction Steps

To a mixture of [3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]phenyl]methanol (1.92 g), methyl 5-hydroxynicotinate (1.0 g), tributylphosphine (1.98 g) and tetrahydrofuran (100 mL) was added 1,1′-(azodicarbonyl)dipiperidine (2.47 g) at room temperature and the mixture was stirred for 15 hrs. The precipitated crystals were removed by filtration. The filtrate was concentrated and the residue was subjected to silica gel column chromatography to give crystals (2.21 g, 79%) of methyl 5-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]nicotinate from a fraction eluted with ethyl acetate-hexane (1:3, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 96-97° C.

Provenance & Evidence