Imidazole → HCID 10977584, compound

HRID 496207Notes

Reaction equation

HRID 496207 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 3 h 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. customat 50° C
  2. washwashed 4 times with water
  3. dry with materialdried over sodium sulfate
  4. customEvaporation of the solvent
  5. customyielded in 6.32 g (96%) of the silylether 513/13 as a colourless liquid

Sources & evidence

ORD record
ord-85b0b90951714299a979dda00fa1378a
Source dataset
uspto-grants-2005_09
Patent number
US06943188B2

Reaction notes

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