Piperidine → 5-{5-[2-(2-Bromoethenyl)-4-(4,5-dihydro-2-oxazolyl)phenoxy]pentyl}-3-methylisoxazole

Participants

Reaction Steps

To a solution of 1.255 g piperidine in 100 ml ether at 0° under nitrogen was added 12 ml n-butyllithium (1.23 m) followed by 5 g triphenylphosphine bromide. The mixture was then stirred two hours at room temperature and 4.78 g 5-{5-[2-formyl-4-(4,5-dihydro-2-oxazolyl)phenoxy]pentyl}-3-methylisoxazole (Example 70) in 35 ml tetrahydrofuran was added dropwise. The reaction mixture was kept overnight at room temperature and worked up by chromatography to give 0.53 g 5-{5-[2-(2-bromoethenyl)-4-(4,5-dihydro-2-oxazolyl)phenoxy]pentyl}-3-methylisoxazole, colorless needles, m.p. 94°-96° C. after recrystallization from isopropyl acetate and hexane.

Provenance & Evidence