Methanol → HCID 14722391, compound

Participants

Reaction Steps

510 mg of metallic sodium was dissolved in 60 ml of methanol. The solution was ice-cooled. Thereto was added 4.25 g of 2-bromo-3-formylamino-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one. The mixture was stirred for 2 hours at 0°-5° C. 600 ml of water was added thereto. The resulting mixture was washed with 200 ml of ethyl acetate, adjusted to pH 4 with 4N hydrochloric acid, and extracted with two 300-ml portions of ethyl acetate. The extracts (the organic layers) were combined, washed with a saturated aqueous sodium chloride solution, and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The resulting crystal was recrystallized from acetonitrile to obtain 2.87 g (yield: 71%) of 3-formylamino-2-methoxy-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one having a melting point of 188° C. (decomposed).

Provenance & Evidence