Imidazole → HCID 178472499, compound

HRID 237325Notes

Reaction equation

HRID 237325 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([OH:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2].N1C=CN=C1.[CH3:18][Si:19](Cl)([CH3:21])[CH3:20]>CN(C)C=O>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([O:12][Si:19]([CH3:21])([CH3:20])[CH3:18])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6397ChlorotrimethylsilaneHCID 178472487HCID 178472487, compound

Product 1

HCID 178472499HCID 178472499, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of cis/trans-4-hydroxycyclohexane carboxylic acid ethyl ester (2:1) (5.0 g, 29 mmol) and imidazole (4.4 g, 64 mmol) in N,N-dimethylformamide (90 ml) was added trimethylsilyl chloride (4.0 ml, 32 mmol) at 0-5° C. Stirring for 1 h at room temperature was followed by partitioning between tert-butyl methyl ether (300 ml) and water (150 ml). The layers were separated. The organic layer was washed with two 150-ml portions of water and one 50-ml portion of brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound (6.7 g, 94%) as colorless oil. MS m/e: 245 (M+H+).

Workup

  1. customby partitioning between tert-butyl methyl ether (300 ml) and water (150 ml)
  2. customThe layers were separated
  3. washThe organic layer was washed with two 150-ml portions of water and one 50-ml portion of brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-43e7839f93f94eb19eb88a49849d5974
Source dataset
uspto-grants-2014_02
Patent number
US08642590B2

Reaction notes

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