Imidazole → HCID 10977584, compound

HRID 584628Notes

Reaction equation

HRID 584628 reaction equation
[CH:1]1([OH:6])[CH2:5][CH2:4][CH:3]=[CH:2]1.[CH:7]([Si:10]([CH:15]([CH3:17])[CH3:16])([CH:12]([CH3:14])[CH3:13])Cl)([CH3:9])[CH3:8].N1C=CN=C1>CN(C=O)C.C(OC(=O)C)C>[CH:1]1([O:6][Si:10]([CH:15]([CH3:17])[CH3:16])([CH:12]([CH3:14])[CH3:13])[CH:7]([CH3:9])[CH3:8])[CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 2201642-Cyclopentene-1-ol

Product 1

HCID 10977584HCID 10977584, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-cyclopentenol (K. Alder, F. H. Flock, Chem. Ber. 1956, 89, 1732.) (2.31 g, 27.5 mmol), (triisopropyl)chlorsilane (5.30 g, 5.9 mL, 27.5 mmol), imidazole (2.06 g, 30.2 mmol) in DMF (50 mL) was stirred at room temperature for 3h and for an additional hour at 50° C. Then the solution was diluted with ethylacetate, washed 4 times with water and dried over sodium sulfate. Evaporation of the solvent yielded in 6.32 g (96%) of the silylether 513/13 as a colourless liquid. No major impurities were visible in the 1H-NMR-spectrum.

Workup

  1. washwashed 4 times with water
  2. dry with materialdried over sodium sulfate
  3. customEvaporation of the solvent
  4. customyielded in 6.32 g (96%) of the silylether 513/13 as a colourless liquid

Sources & evidence

ORD record
ord-829120dea57a4da58f3d97d0d054cb3f
Source dataset
uspto-grants-2005_08
Patent number
US06927222B2

Reaction notes

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