Tetrahydrofuran → Cyclohexanemethanol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, cis-

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Reaction Steps

Lithium aluminum hydride (696 mg, 18.4 mmol) was added to a tetrahydrofuran solution (25 ml) of methyl 4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexanecarboxylate (2.50 g, 9.18 mmol) under ice-cooling. The resulting mixture was warmed up to room temperature and then stirred overnight. After completion of the reaction, water and a 15% aqueous sodium hydroxide solution were added thereto and stirred. The solid formed was removed by filtration, and the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was purified by a silica gel column chromatography (hexane-ethyl acetate=1:1) to obtain (4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)methanol (2.08 g, 93%).

Provenance & Evidence