Hydrochloric Acid → HCID 68550659, compound

Participants

Reaction Steps

Acetylacetone (10.3 μL, 100 μmol) and boron trioxide (25 mg, 0.40 mmol) was placed in a 20 mL reaction vessel, and dissolved in 0.45 mL of ethyl acetate. To the stirring solution at 80° C. were added 1,4-benzodioxane-6-carboxaldehyde (41 mg, 0.25 mmol) and tri-n-butyl borate (57 μL, 0.21 mmol), successively. After the reaction mixture was stirred for 2 h at the same temperature, n-butylamine (22 μL, 0.22 mmol) was added with additional stirring for 1 h. The reaction mixture was treated with a 1:1 solution (3 mL) of 1N HCl and brine at room temperature, and was stirred at 50° C. for 5 min to 1 h (if necessary, the reaction mixture was neutralized with saturated NaHCO3 aqueous solution). The organic layer was purified directly by silica gel column chromatography (eluting with hexane/ethyl acetate or chloroform/methanol) to obtain the title compound as a solid (20.0 mg, 51%) having the following characteristics.

Provenance & Evidence