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

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Reaction Conditions

Reaction Steps

At 0° C., 8.1 g (29.7 mmol) of methyl 4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexanecarboxylate (trans/cis mixture) as a solution in 50 ml of THF were added dropwise to a solution of 50 ml (100 mmol) of lithium aluminium hydride (2M in THF). The mixture was stirred at 0° C. for another 1 h and at RT for another 2 h. 3.8 ml of water, 3.8 ml of aqueous sodium hydroxide solution (15%) and 11.4 ml of water were then added to the reaction in succession, and the precipitate was filtered off. The organic phase was washed with 50 ml of saturated aqueous sodium chloride solution, dried over magnesium sulphate and filtered, and the solvent was removed under reduced pressure. Yield: 7.00 g (92% of theory)

Provenance & Evidence