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

HRID 1269914Notes

Reaction equation

HRID 1269914 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[Si:12]([O:19][CH:20]1[CH2:25][CH2:24][CH:23]([C:26](OC)=[O:27])[CH2:22][CH2:21]1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].[OH-].[Na+]>O>[Si:12]([O:19][CH:20]1[CH2:21][CH2:22][CH:23]([CH2:26][OH:27])[CH2:24][CH2:25]1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22167752Methyl trans-4-[(tert-butyldimethylsilyl)oxy]cyclohexanecarboxylate

Product 1

HCID 57999111Cyclohexanemethanol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, cis-Yield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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%).

Workup

  1. temperaturecooling
  2. stirringstirred
  3. customThe solid formed
  4. customwas removed by filtration
  5. distillationthe solvent was distilled off under reduced pressure
  6. customto obtain a crude product
  7. customThe crude product was purified by a silica gel column chromatography (hexane-ethyl acetate=1:1)

Sources & evidence

ORD record
ord-4225fa700ead445c804a93f54c517eee
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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