Tetrahydrofuran → HCID 58047413, compound

Participants

Reaction Steps

To a solution of 1-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1-benzofuran-3-yl]ethanone (1.19 g, 3.91 mmol) obtained in Reference Example 19 in THF (6 mL) was added 1 M tetrabutylammonium fluoride THF solution (7.82 mL, 7.82 mmol). The mixture was stirred at room temperature for 2 hr. To the reaction mixture was added aqueous saturated ammonium chloride, and the mixture was extracted twice with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solution was passed through silica gel. The solvent was evaporated under reduced pressure to give an alcohol form (965 mg). To a solution of the obtained alcohol form (965 mg), triphenylphosphine (1.54 g, 5.88 mmol) and p-ethoxyphenol (825 mg, 5.88 mmol) in anhydrous THF (8 mL) was added dropwise 40% diethyl azodicarboxylate-toluene solution (2.7 mL, 5.88 mmol) and the mixture was stirred at room temperature for 10 min. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=7:3) to give the title compound (117 mg, yield from 1-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1-benzofuran-3-yl]ethanone 10%) as an oil.

Provenance & Evidence