Dimethylformamide → 7-Methoxy-3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)naphtho[1,2-c]isoxazol-5(4H)-one

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 7-methoxy-3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazole (Preparation 66A, 0.103 g, 0.250 mmol) and cuprous iodide (0.476 mg, 0.0025 mmol) in acetonitrile (2.0 mL) at room temperature [note: the reactant was sparingly soluble in acetonitrile, so dimethyl formamide (0.5 ml) was added to solubilize the reactant] was added t-butyl hydroperoxide (0.250 mL, 1.50 mmoL). The reaction mixture was heated at 50° C. overnight. An additional aliquot of t-butyl hydroperoxide (0.250 mL, 1.50 mmol) was added, and the reaction was heated at 50° C. overnight. A small change in the amount of product was noted, so an additional aliquot of t-butyl hydroperoxide (0.250 mL, 1.50 mmol) was added. The reaction mixture was heated at 50° C. overnight. The reaction mixture was concentrated in vacuo, and the crude mixture was chromatographed using reverse-phase preparative HPLC to give the product [39 mg, 0.094 mmol, 36% yield] as a tan solid. The product had an HPLC ret. time=3.90 min. (condition B). LC/MS M+1=427.10.

Provenance & Evidence