N,N,N',N'-Tetramethylethylenediamine → 4-Vinyloxyethoxyphenyldiphenylsulfonium perfluorobutanesulfonate salt

HRID 747642Notes

Reaction equation

HRID 747642 reaction equation
[F:1][C:2]([F:17])([S:13]([O-:16])(=[O:15])=[O:14])[C:3]([F:12])([F:11])[C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6].[OH:18][C:19]1[CH:24]=[CH:23][C:22]([S+:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)CCN(C)C.[CH:52]([O:54][CH2:55][CH2:56]Cl)=[CH2:53]>CS(C)=O>[F:17][C:2]([F:1])([S:13]([O-:16])(=[O:15])=[O:14])[C:3]([F:11])([F:12])[C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6].[CH:52]([O:54][CH2:55][CH2:56][O:18][C:19]1[CH:24]=[CH:23][C:22]([S+:25]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:21][CH:20]=1)=[CH2:53]

Participants

6

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 80742-Chloroethyl vinyl etherHCID 11430Potassium CarbonateHCID 22481373HCID 22481373, compound

Product 1

HCID 875724424-Vinyloxyethoxyphenyldiphenylsulfonium perfluorobutanesulfonate salt

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

4-Hydroxyphenyldiphenylsulfonium perfluorobutanesulfonate salt (52.2 g), potassium carbonate (18.0 g), and N,N,N′,N′-tetramethylethylenediamine (1.05 g) were dissolved in dimethyl sulfoxide (26.1 g). Chloroethyl vinyl ether (13.9 g) was added to the solution, followed by heating to 80° C. The reaction mixture was stirred for 15 hours and cooled to 30° C. or lower. After removal of solid through filtration, water (100 g) was added to the filtrate, and the aqueous layer was washed three times with hexane (100 g). To the washed aqueous layer, dichloromethane (209 g) and water (260 g) were added under stirring, whereby the target substance was extracted to the dichloromethane layer. The organic layer was repeatedly washed with distilled water until the pH of the separated aqueous layer was shifted to 7. The solvent was removed by means of a rotary evaporator, to thereby yield 69.9 g of an oily substance. Through 1H-NMR and ion chromatography, the substance was identified to be 4-vinyloxyethoxyphenyldiphenylsulfonium perfluorobutanesulfonate salt.

Workup

  1. temperaturecooled to 30° C.
  2. customAfter removal of solid
  3. filtrationthrough filtration, water (100 g)
  4. additionwas added to the filtrate
  5. washthe aqueous layer was washed three times with hexane (100 g)
  6. additionTo the washed aqueous layer, dichloromethane (209 g) and water (260 g) were added
  7. stirringunder stirring
  8. extractionwhereby the target substance was extracted to the dichloromethane layer
  9. washThe organic layer was repeatedly washed with distilled water until the pH of the separated aqueous layer
  10. customThe solvent was removed by means of a rotary evaporator

Sources & evidence

ORD record
ord-696ebd76553b46fc971b1445e3da5738
Source dataset
uspto-grants-2008_07
Patent number
US07396960B2

Reaction notes

Loading…