Hydrochloric Acid → HCID 178439669, compound

Participants

Reaction Steps

A mixture of 2.5 g of 4-([3-hydroxy-4-(2-hydroxybenzoyl)-2-propylphenoxy]methyl)benzonitrile and 7.98 g of tri n-butylstannylazide in 50 ml of tetrahydrofuran were heated at reflux for 3 days. An additional 2.66 g of the azide reagent were added and the reaction was heated at reflux for an additional 4 days. The reaction was cooled and 10 ml of a 10:1 methanol/1N hydrochloric acid mixture were added. After stirring for 1 hour, the mixture was poured into an ethyl acetate/water mixture and the layers were separated. The organic layer was washed once with water and once with a saturated sodium chloride solution, dried over magnesium sulfate, filtered, and evaporated in vacuo. The resulting oil was purified by high pressure liquid chromatography eluting with a 40-75% ethyl acetate in hexane gradient containing 0.5% acetic acid. The appropriate fractions were combined, evaporated, and crystallized from ethyl acetate/hexane to provide 1.72 g of the desired title product, m.p. 186°-187° C.

Provenance & Evidence