Tetrahydrofuran → 1-Benzyloxymethyl-3-hydroxyphenylmethyl-5-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

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Reaction Steps

To 87 ml of dehydrated tetrahydrofuran solution containing 3.60 g (8.71 mmol) of 1-benzyloxymethyl-3-formyl-5-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo-[2,3-d]pyridazin-4-one obtained in Reference example 33-(d) were added 12.2 ml of 1M phenyl magnesium bromide tetrahydrofuran solution under ice-cooling and under argon atmosphere, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, to the reaction mixture were added a saturated aqueous solution of ammonium chloride and a saturated aqueous solution of sodium chloride, and the mixture was extracted with ethyl acetate. The organic layer after separation was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=4:1→1:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 3.12 g of the title compound as a yellowish oil. (Yield: 73%)

Provenance & Evidence