反応 #1946563

反応方程式

sodium hydroxide

cyclohexylmercaptan

ethanol

sodium hydroxide

2-bromo-1-indanone

→

2-(cyclohexylthio)-1-indanone

収率 23.0%

溶媒

ether

ether

water

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   温度refluxed
3. 3
   温度under heating
4. 4
   温度the solution was cooled
5. 5
   workup.ADDITIONwas added dropwise to the cooled solution
6. 6
   抽出for extracting an organic phase
7. 7
   洗浄the ether layer was sequentially washed with an aqueous sodium chloride solution and water
8. 8
   乾燥After the ether layer was dried with magnesium sulfate
9. 9
   その他the ether was evaporated under vacuum
10. 10
    その他The residue was isolated
11. 11
    その他purified through a silica gel column (elute: hexane/ethyl acetate=9/1)

実験手順

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%).

出典