p-Toluenesulfonic acid → HCID 15868597, compound

Participants

Reaction Steps

0.91 g of 1-chloro-4-morpholino-2-naphthol are allowed to react with 0.95 g of 1-(p-methoxyphenyl)-1-phenyl-2-propyn-1-ol in 30 ml of THF under reflux for 4 hours in the presence of 0.72 g of p-toluene sulfonic acid. The solution is then neutralized with 30 ml of 1N sodium hydroxide and then extracted twice with 30 ml of toluene. The organic phases are evaporated and then the photochrome is separated by chromatography on an alumina column in eluting with a mixture of ethyl acetate/diisopropyl ether (10/90). 250 mg of 3-(p-methoxyphenyl)-3-phenyl-6-morpholino-[3H]-naphtho-[2,1-b]pyran (compound II) are thus obtained. Its structure is confirmed by 1H NMR spectroscopy.

Provenance & Evidence