Ethanol → HCID 12067525, compound

HRID 1859381Notes

Reaction equation

HRID 1859381 reaction equation
[CH:1]1([SH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)C.[OH-].[Na+].Br[CH:14]1[CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:23]>CCOCC.O>[CH:1]1([S:7][CH:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:23])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 702EthanolHCID 14798Sodium Hydroxide2×HCID 15290CyclohexanethiolHCID 1372032-Bromo-1-indanone

Product 1

HCID 12067525HCID 12067525, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

After 5.5 g of cyclohexylmercaptan was dissolved into 50 ml of ethanol, 1.97 g of sodium hydroxide was added thereto and refluxed under heating. After the complete dissolving of the sodium hydroxide, the solution was cooled on standing. After 10 g of 2-bromo-1-indanone (available from Aldrich Corporation) dissolved in 10 ml of ether was added dropwise to the cooled solution and stirred for three hours at room temperature, the reaction mixture was poured into 300 ml of cold water. After 200 ml of ether was added thereto for extracting an organic phase, the ether layer was sequentially washed with an aqueous sodium chloride solution and water. After the ether layer was dried with magnesium sulfate, the ether was evaporated under vacuum. The residue was isolated and purified through a silica gel column (elute: hexane/ethyl acetate=9/1) to provide 2.4 g of 2-(cyclohexylthio)-1-indanone (yield: 23%). Then, 2 g of the 2-(cyclohexylthio)-1-indanone was dissolved into 6 ml of nitromethane, and 10.7 g of methyl iodide was added thereto and stirred at room temperature. After an hour, 40 ml of nitromethane dissolving 2.09 g of silver trifluoromethanesulfonate was added dropwise thereto. After the stirring for 18 hours at room temperature, precipitated silver iodide was filtrated and a filtrate was concentrated to about one-third under vacuum. After the residue was added dropwise to 250 ml of ether, a precipitated sulfonium salt was filtered. The precipitated sulfonium salt was recrystalized from ethyl acetate-ethanol to provide 2.42 g of the sulfonium salt having the above structure (yield: 73%).

Workup

  1. additionwas added
  2. temperaturerefluxed
  3. temperatureunder heating
  4. temperaturethe solution was cooled
  5. additionwas added dropwise to the cooled solution
  6. extractionfor extracting an organic phase
  7. washthe ether layer was sequentially washed with an aqueous sodium chloride solution and water
  8. dry with materialAfter the ether layer was dried with magnesium sulfate
  9. customthe ether was evaporated under vacuum
  10. customThe residue was isolated
  11. custompurified through a silica gel column (elute: hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-cac4f8c1cb404488b9537c142a9e8726
Source dataset
uspto-grants-2003_03
Patent number
US06528232B1

Reaction notes

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