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

HRID 475376Notes

Reaction equation

HRID 475376 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([OH:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2].N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].C(OCC)C>CN(C)C=O>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([O:12][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 28928tert-Butyldimethylsilyl chlorideHCID 86973Ethyl 4-hydroxycyclohexanecarboxylate

Product 1

HCID 23144129Ethyl 4-((tert-butyldimethylsilyl)oxy)cyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxy-cyclohexanecarboxylic acid ethyl ester (10.32 g, 59.92 mmol) in dimethylformamide (50 mL) was added imidazole (8.16 g, 119.8 mmol), followed by tert-butyldimethylsilyl chloride (9.94 g, 65.9 mmol). The resulting mixture was stirred at room temperature for 16 hours. Diethyl ether was added (150 mL), and the mixture was washed with 1M HCl (150 mL). The aqueous layer was extracted with diethyl ether (150 mL). The combined organic layers were washed with 1M HCl (100 mL) and saturated sodium chloride solution (100 mL), dried over magnesium sulfate, filtered and concentrated to afford a clear oil. MS (CI) m/z 287 (M+1)+

Workup

  1. washthe mixture was washed with 1M HCl (150 mL)
  2. extractionThe aqueous layer was extracted with diethyl ether (150 mL)
  3. washThe combined organic layers were washed with 1M HCl (100 mL) and saturated sodium chloride solution (100 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford a clear oil

Sources & evidence

ORD record
ord-8baec8bd86924d6ca62f006ff7008aeb
Source dataset
uspto-grants-2014_01
Patent number
US08637546B2

Reaction notes

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