Ethanol → 2-Methanesulfonyloxymethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one

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Reaction Steps

2-Hydroxymethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one (1.2 g) was added to anhydrous pyridine (24 ml). The mixture was stirred on ice, during which methanesulfonylchloride (625 mg) was added thereto, followed by stirring at room temperature for 100 minutes. Methanesulfonylchloride (283 mg) was added again and stirred at the same temperature for 50 minutes. After completion of the reaction, a small amount of ethanol was added, and the mixture was brought to dryness under reduced pressure. The residue was dissolved in a solvent mixture of chloroform and methanol (10:1), washed with diluted HCl, sodium bicarbonate water, and aqueous NaCl solution in this order, and dried. When the solvent was evaporated, 1.6 g (quantitative assay) of the title compound was obtained. This substance was recrystallized from a solvent mixture of chloroform-n-hexane, obtaining colorless powdery crystals having a melting point of 200°-203° C.

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