Sodium Chloride → 1-Methyl-8-benzyloxy-3,4-dihydrocarbostyril-5-ol tetrahydropyranyl ether

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Reaction Steps

5 g of 8-benzyloxy-3,4-dihydrocarbostyril-5-ol-detrahydropyranyl ether (IV) was dissolved in 100 ml of anhydrous dimethylformamide, and 810 g of sodium hydride was slowly added to the solution while stirring, followed by stirring at room temperature for 1 hour. 1.05 ml of methyl iodide was further added dropwise thereto followed by stirring at the same temperature for 2 hours. The reaction mixture was poured into a large volume of a saturated aqueous solution of sodium chloride, extracted with chloroform, washed with water and dried over anhydrous potassium carbonate. The chloroform was evaporated under reduced pressure, and the residue was recrystallized from ligroin to obtain 1.42 g of 1-methyl-8-benzyloxy-3,4-dihydrocarbostyril-5-ol-tetrahydropyranyl ether as colorless needle-like crystals having a melting point of 110.5°-111.5° C.

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