Imidazole → cis-4-((t-Butyldimethylsilyl)oxy)cyclohexan-1-ol

HRID 1773489Notes

Reaction equation

HRID 1773489 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH:9]1([OH:16])[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11][CH2:10]1.N1C=CN=C1>CN(C)C=O.O1CCCC1.[Cl-].[Na+].O>[C:4]([Si:1]([CH3:3])([CH3:2])[O:15][CH:12]1[CH2:13][CH2:14][CH:9]([OH:16])[CH2:10][CH2:11]1)([CH3:7])([CH3:6])[CH3:5]

Participants

7

Reactant 3

HCID 795ImidazoleHCID 111621,4-CyclohexanediolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 554539cis-4-((t-Butyldimethylsilyl)oxy)cyclohexan-1-olYield 66%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of tert-butyldimethylsilyl chloride (1.5 g, 9.9 mmol) in anhydrous N,N-dimethylformamide (5 mL) was added, dropwise, at 0° C., to a solution of 1,4-cyclohexanediol (1.0 g, 8.6 mmol) and imidazole (1.5 g, 22.0 mmol) in anhydrous tetrahydrofuran (5 mL). After completion of the addition brine was added and the resulting mixture was extracted 3 times with ethyl acetate. The combined organic extracts were washed with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified on a silica gel plug (hexane/EtOAc, 80/20) to afford 1.3 g (66% yield) of 4-(tert-butyl-dimethyl-silanyloxy)-cyclohexanol as a colorless oil.

Workup

  1. customat 0° C.
  2. additionwas added
  3. extractionthe resulting mixture was extracted 3 times with ethyl acetate
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe crude residue was purified on a silica gel plug (hexane/EtOAc, 80/20)

Sources & evidence

ORD record
ord-07847fa883c7402c8d6067425c351b9a
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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