Methyl iodide → 1,3-Benzoxathiol-2-one, 5-methoxy-

Participants

Reaction Steps

With cooling with ice, 60% oily sodium hydride (3.14 g) was added to a 1,2-dimethoxyethane (100 mL) solution of 5-hydroxy-1,3-benzoxathiol-2-one (10 g, 59.5 mmol), and stirred for 10 minutes. With cooling with ice, methyl iodide (37 mL) was added to the reaction liquid, and stirred for 2 hours with cooling with ice and further for 6 hours at room temperature. Aqueous saturated ammonium chloride solution was added to the reaction liquid, and extracted three times with chloroform. The organic layer was dried with magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/2) to obtain the intended compound (7.8 g, 72%) as a white solid.

Provenance & Evidence