Tetrahydrofuran → Sulfonium, triphenyl-, 1,1,1-trifluoromethanesulfonate (1:1)

Temperature

-78 °C

2.0 g of phenyl sulfoxide dissolved in 20 mL dichloromethane was cooled to -78° C. and then, 2.3 mL trimethylsilyl triflate was slowly added to the mixture for more than 5 minutes. The reacting mixture was stirred at the same temperature for 10 minutes and with the gradual increase of reaction temperature, stirred at 0° C. for 30 minutes. The solution was again cooled to -78° C. and 10 mL tetrahydrofuran solution of 2.0 M phenyl magnesium bromide was slowly added to the reacting solution. The reacting mixture was stirred at the same temperature for 30 minutes and further stirred at 0° C. for 30 minutes. The reaction was completed in 30 mL of 3% triflic acid aqueous solution. The reactant was diluted with 200 mL ether and extracted two times with 30 mL of triflic acid aqueous solution. The aqueous solution, so extracted, was further extracted three times with 30 mL chloroform. After collection of the organic layer, the solution was dried over anhydrous Na2SO4 and filtrated to remove the solvent. Thus, 1.9 g of triphenyl sulfonium triflate (yield: 50%) was obtained as a white solid.

1. temperaturewith the gradual increase of reaction temperature
2. stirringstirred at 0° C. for 30 minutes
3. temperatureThe solution was again cooled to -78° C.
4. stirringThe reacting mixture was stirred at the same temperature for 30 minutes
5. stirringfurther stirred at 0° C. for 30 minutes
6. extractionextracted two times with 30 mL of triflic acid aqueous solution
7. extractionThe aqueous solution, so extracted
8. extractionwas further extracted three times with 30 mL chloroform
9. customAfter collection of the organic layer
10. dry with materialthe solution was dried over anhydrous Na2SO4
11. filtrationfiltrated
12. customto remove the solvent

ORD record

ord-151f411783c244c3b1a19edf7fb18644

Source dataset

uspto-grants-2000_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06111143