Triphenylphosphine → 2-Methoxy-5-[3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridine

Participants

Reaction Steps

To a suspension of 0.81 g (3.9 mmol) of 4-(5-methyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenol, 0.8 g (1.2 eq) of 2-methoxy-5-(3-hydroxypropyl)-pyridine, 1.4 g (1.2 eq) of triphenylphosphine in 70 ml of methylene chloride under nitrogen at 5° C. was added in portions 0.88 g (1.2 eq) of DEAD. The mixture was concentrated in vacuo, the residue was triturated with ether, filtered, and the crude product was purified by MPLC (50 id,Kieselgel 60 column, hexane/ethyl acetate, 2:1) and recrystallization from isopropyl acetate/hexane to afford 1 g (71.4%) of 2-methoxy-5-[3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridine, as a white powder, m.p. 71°-73° C.

Provenance & Evidence