Methyl iodide → HCID 10808426, compound

Participants

Reaction Conditions

Reaction Steps

2.50 g (7.24 mmol) of the 8-tert-butyldimethylsilyloxy-3-cyanomethyl-6-methoxy-1-oxo-1H-2-benzopyran obtained in Example 5 was dissolved in 80 ml of methylene chloride. 100 ml of a 1M aqueous solution of sodium hydroxide was added thereto, and the resulting mixture was cooled to 0° C. While this mixture was being vigorously stirred, 584 mg (1.81 mmol) of tetrabutylammonium fluoride and then 10 ml of methylene chloride containing 0.92 ml (14.47 mmol) of methyl iodide were added thereto, followed by stirring at 0° C. for 1 hour. Moreover, 10 ml of methylene chloride containing 0.92 ml (14.47 mmol) of methyl iodide was added thereto, followed by stirring for 30 minutes. After completion of the reaction, the methylene chloride layer was separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography [using 130 g of Wako Gel C-200 and hexane/ethyl acetate (5:1)]. Thus, 1.01 g of the title compound was obtained in a 39% yield.

Provenance & Evidence