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

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Reaction Steps

200 mg (0.59 mmol) of the crude product from Example 9A (80% pure) are dissolved in 1.5 ml of diethyl ether. At RT, this solution is added dropwise to a suspension of 13.4 mg (0.35 mmol) of lithium aluminum hydride in 1.5 ml of diethyl ether. The mixture is stirred at RT for 20 h. 12 μl of water, 12 μl of 15% strength aqueous potassium hydroxide solution and 3 ml of diethyl ether are then added, and the mixture is stirred at RT for 30 min. The reaction mixture is then filtered through a cartridge charged with 2.4 g of silica gel and 2.4 g of Extrelut (mobile phase: dichloromethane/ethanol 10:1). The solvent is removed on a rotary evaporator and the residue is purified chromatographically on silica gel 60 (mobile phase: gradient cyclohexane/ethyl acetate 20:1→10:1).

Provenance & Evidence