Imidazole → Ethyl 4-((tert-butyldimethylsilyl)oxy)cyclohexanecarboxylate

HRID 337487Notes

Reaction equation

HRID 337487 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].O>CN(C=O)C>[Si:18]([O:1][CH:2]1[CH2:3][CH2:4][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:7]1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 86973Ethyl 4-hydroxycyclohexanecarboxylate

Product 1

HCID 23144129Ethyl 4-((tert-butyldimethylsilyl)oxy)cyclohexanecarboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 4-hydroxycyclohexanecarboxylate (3.44 g, 20.0 mmol) was dissolved in DMF (7 mL), and imidazole (3.40 g, 50.0 mmol) and tert-butyldimethylsilyl chloride (3.62 g, 24 mmol) were added thereto, followed by stirring overnight at room temperature. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=10:1) to afford ethyl 4-(tert-butyldimethylsilyloxy)cyclohexane-carboxylate (5.73 g, 100%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled away under reduced pressure
  4. customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-a640d8c5b93c4938a3a8d1b37119fbb7
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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