Imidazole → 5-(Tert-butyl)dimethylsilyloxy-1-cyclooctanone

HRID 498099Notes

Reaction equation

HRID 498099 reaction equation
[CH:1]1(O)[CH2:8][CH2:7][CH2:6][CH:5]([OH:9])[CH2:4][CH2:3][CH2:2]1.[CH3:11][C:12]([CH3:14])=O.OS(O)(=O)=O.O=[Cr](=O)=O.S(=O)(=O)(O)O.[Cr](O)(O)(=O)=O.N1C=CN=[CH:35]1.[C:39]([Si:43](Cl)(C)[CH3:44])(C)(C)C.C(=O)(O)[O-].[Na+].[OH2:52]>CC(C)=O.CN(C)C=O.CC(O)C>[C:12]([CH:8]1[CH2:1][CH2:2][CH2:3][C:4](=[O:52])[CH:5]([O:9][SiH:43]([CH3:44])[CH3:39])[CH2:6][CH2:7]1)([CH3:14])([CH3:35])[CH3:11]

Participants

12

Reactant 8

HCID 795ImidazoleHCID 962WaterHCID 1118Sulfuric AcidHCID 24425Chromic AcidHCID 28928tert-Butyldimethylsilyl chlorideHCID 90092cis-Cyclooctane-1,5-diolHCID 516892Sodium BicarbonateHCID 131709961Jones' reagent

Product 1

HCID 1317251665-(Tert-butyl)dimethylsilyloxy-1-cyclooctanone

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent

Procedure

9.8 g of 1,5-cyclooctanediol was dissolved in 150 ml of acetone, and to the solution was added Jones reagent prepared with 11.5 ml of sulfuric acid, 13 g of chromic acid and 20 ml of water. The solution was stirred at room temperature for fifteen minutes. To the reaction solution was added 2 ml of 2-propanol. Then, the solution was filtered through Celite. The residue was washed with dichloromethane and the washing solution was combined with the filtrate. The filtrate was washed with water and a saturated saline solution, and dried over anhydrous sodium sulfate. The solvent was evaporated, to afford a white solid. The crude product was dissolved in 200 ml of dimethylformamide. To the solution were added 6.6 g of imidazole and 12 g of tert-butylchlorodimethysilane. The reaction solution was stirred at room temperature overnight, and then cooled in an ice bath. To the resulting solution was added a saturated sodium bicarbonate aqueous solution. The reaction solution was extracted with diethylether, washed with a saturated saline solution, and dried over anhydrous sodium sulfate. The solvent was evaporated. The residue was subject to column chromatography on silica gel, and the eluate with ethyl acetate-hexane (1:9) was collected, to afford 13.6 g of the titled compound (a) as colorless liquid.

Workup

  1. filtrationThen, the solution was filtered through Celite
  2. washThe residue was washed with dichloromethane
  3. washThe filtrate was washed with water
  4. dry with materiala saturated saline solution, and dried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customto afford a white solid
  7. stirringThe reaction solution was stirred at room temperature overnight
  8. temperaturecooled in an ice bath
  9. extractionThe reaction solution was extracted with diethylether
  10. washwashed with a saturated saline solution
  11. dry with materialdried over anhydrous sodium sulfate
  12. customThe solvent was evaporated
  13. customthe eluate with ethyl acetate-hexane (1:9) was collected

Sources & evidence

ORD record
ord-8fd9a2bf5b7548cd9920c3746282296c
Source dataset
uspto-grants-2005_09
Patent number
US06949585B2

Reaction notes

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