Imidazole → Methyl trans-4-[(tert-butyldimethylsilyl)oxy]cyclohexanecarboxylate

HRID 1269913Notes

Reaction equation

HRID 1269913 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH2:3]1.N1C=CN=C1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].CCCCCC.C(OCC)(=O)C>CN(C)C=O.O>[Si:17]([O:1][CH:2]1[CH2:3][CH2:4][CH:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:6][CH2:7]1)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 87117Methyl 4-hydroxycyclohexanecarboxylateHCID 21226206Ethyl acetate hexane

Product 1

HCID 22167752Methyl trans-4-[(tert-butyldimethylsilyl)oxy]cyclohexanecarboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 4-hydroxycyclohexane-carboxylate (a cis/trans mixture, 5.00 g, 31.6 mmol) and imidazole (4.30 g, 63.2 mmol) in dimethylformamide (20 ml) was added t-butyldimethylsilyl chloride (5.72 g, 37.9 mmol) at room temperature, and stirred at the same temperature for 5 hours. After completion of the reaction, an ethyl acetate/toluene (1/1) solution and water were added thereto, and the organic layer was collected, dried over sodium sulfate and distilled under reduced pressure to remove the solvent, whereby methyl 4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexane-carboxylate (8.66 g, 100%) was obtained.

Workup

  1. customAfter completion of the reaction
  2. customthe organic layer was collected
  3. dry with materialdried over sodium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent

Sources & evidence

ORD record
ord-716376d0dae949bb88f63dfabc6abb16
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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