Sulfuric Acid → HCID 21906966, 화합물

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A mixture of 1-phenylcyclobutanecarboxylic acid (10) and acetic acid (20 ml) and H2SO4 (20 ml) and KNO3 (1.1 eq) was stirred at 0° C. for 20 min. The mixture was warmed to RT and stirred overnight. The mixture was poured on ice and stirred until all ice melted. The precipitate was filtered and used for next step without further purification. The above product (5 g) was dissolved into THF and stirred at 0° C., NaBH4 (3 eq) was added slowly to the reaction followed by slowly addition of BF3.Et2O (3 eq). The reaction was stirred at RT overnight and quenched with 1 N NaOH slowly until bubble ceased. The solution was extracted with EtOAc and washed with H2O followed by brine, dried over Na2SO4 and evaporated. The residue was purified by column chromatography to give [(4-nitrophenyl)cyclobutyl]methane-1-ol as an oil.

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