Imidazole → 1-Ethynyl-1-triethylsiloxycyclopentane

HRID 2416151Notes

Reaction equation

HRID 2416151 reaction equation
CN(C)C=O.[C:6]([C:8]1([OH:13])[CH2:12][CH2:11][CH2:10][CH2:9]1)#[CH:7].N1C=CN=C1.[CH2:19]([Si:21]([CH2:25][CH3:26])([CH2:23][CH3:24])Cl)[CH3:20]>CCCCCC>[C:6]([C:8]1([O:13][Si:21]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:19][CH3:20])[CH2:12][CH2:11][CH2:10][CH2:9]1)#[CH:7]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 13819ChlorotriethylsilaneHCID 870741-Ethynylcyclopentanol

Product 1

HCID 226391411-Ethynyl-1-triethylsiloxycyclopentaneYield 83.4%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a dimethylformamide solution (49.5 ml) of 1-ethynyl-1-hydroxycyclopentane (5.45 g, 49.5 mmol) were added imidazole (6.74 g, 99.0 mmol) and triethylchlorosilane (9.97 ml, 59.4 mmol) at room temperature, followed by stirring for 30 minutes. The reaction solution was added to a mixture of n-hexane and a saturated aqueous sodium bicarbonate solution, and the organic layer was separated. The aqueous layer was extracted with hexane, and the organic layers were combined, washed with a saturated aqueous sodium bicarbonate solution and dried over anhydrous magnesium sulfate. After filtration, the filtrate was evaporated under reduced pressure to give the title compound (9.26 g).

Workup

  1. customa saturated aqueous sodium bicarbonate solution, and the organic layer was separated
  2. extractionThe aqueous layer was extracted with hexane
  3. washwashed with a saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-508373607b424baa800aadb00ec4ec19
Source dataset
uspto-grants-2004_11
Patent number
US06822112B1

Reaction notes

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