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

HRID 855850Notes

Reaction equation

HRID 855850 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-6bce405dadbb4a35b32bec1d2a76c20c
Source dataset
uspto-grants-2007_08
Patent number
US07262207B2

Reaction notes

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