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

HRID 56828Notes

Reaction equation

[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15](OC)=[O:16])[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[Si:1]([O:8][CH:9]1[CH2:10][CH2:11][CH:12]([CH2:15][OH:16])[CH2:13][CH2:14]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

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)

Workup

filtrationthe precipitate was filtered off
washThe organic phase was washed with 50 ml of saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulphate
filtrationfiltered
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-907c5bbd68a34d3ca94df9540bf684d0
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434690B2

Reaction notes

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