1-[4-(azidomethyl)phenyl]ethanone

反応条件: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of aluminum lithium hydride (5.31 g) in tetrahydrofuran (500 ml) was added dropwise a solution of (4-azidomethylphenyl) methyl ketone (8.18 g) in tetrahydrofuran (100 ml) at below 5° C. over 30 min. The mixture was stirred at 30° C. for 2 hr. A saturated aqueous sodium sulfate solution (30 ml) was added and the mixture was stirred for 1 hr. The insoluble matter was filtered off and the solvent was evaporated. The obtained residue was dissolved in ethyl acetate (100 ml), 2N aqueous sodium hydroxide solution (30 ml) and water (70 ml). Thereto was added dropwise acetic anhydride (4.8 ml) with vigorous agitation at 10-15° C. over 10 min. The mixture was stirred at room temperature for 1 hr. The organic layer was separated and the aqueous layer was extracted with ethyl acetate and combined with the organic layer. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (elution solvent; methanol:chloroform=3:97, later 5:95) to give the title compound (5.37 g) as a rather brown oil. the mixture was stirred for 1 hr The insoluble matter was filtered off the solvent was evaporated The obtained residue was dissolved in ethyl acetate (100 ml) Thereto was added dropwise acetic anhydride (4.8 ml) with vigorous agitation at 10-15° C. over 10 min The mixture was stirred at room temperature for 1 hr The organic layer was separated the aqueous layer was extracted with ethyl acetate The organic layer was washed with saturated brine dried over anhydrous sodium sulfate The solvent was evaporated the obtained residue was purified by silica gel column chromatography ( elution solvent