Water → tert-butyl 9-(2-formyl-3-furyl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 9-bromo-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (1.48 g, 4.50 mmol), 2-formylfuran-3-boronic acid pinacol ester (1.00 g, 4.50 mmol), saturated aqueous sodium carbonate solution (20 ml), and tetrakis(triphenylphosphine)palladium(0) (147 mg, 0.127 mmol) in ethylene glycol dimethyl ether (25 ml) was stirred under a nitrogen atmosphere at 85° C. for 12 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the desired product (750 mg, 48.4%) as an oil.

Provenance & Evidence