Dimethyl Sulfoxide → HCID 86641513, compound

HRID 2284890Notes

Reaction equation

HRID 2284890 reaction equation
[OH-].[Na+].[O-:3][S:4]([C:7]([F:10])([F:9])[F:8])(=[O:6])=[O:5].[OH:11][C:12]1[CH:17]=[CH:16][C:15]([S+:18]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:14][CH:13]=1.CS(C)=O.Cl[CH2:37][CH2:38][O:39][CH:40]=[CH2:41].[CH3:42][CH2:43][O:44][CH2:45][CH3:46]>O>[O-:6][S:4]([C:7]([F:10])([F:9])[F:8])(=[O:5])=[O:3].[CH:40]([O:39][CH2:38][CH2:37][O:11][C:12]1[CH:17]=[CH:16][C:15]([S+:18]([C:25]2[CH:26]=[CH:27][C:28]([O:31][CH2:46][CH2:45][O:44][CH:43]=[CH2:42])=[CH:29][CH:30]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:14][CH:13]=1)=[CH2:41]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 3283Diethyl Ether2×HCID 80742-Chloroethyl vinyl etherHCID 14798Sodium HydroxideHCID 18411305HCID 18411305, compound

Product 1

HCID 86641513HCID 86641513, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A 3-neck-round bottom flask was fitted with a condenser, an addition funnel, nitrogen source, and a magnetic bar. Sodium hydroxide (8.64 g, 0.216 mol), bis(4-hydroxyphenyl)phenylsulfonium triflate (16 g, 0.036 mol) and DMSO (90 ml) were added to a round bottom flask under N2. The mixture was heated to 60° C. for 1 hour. 2-chloroethyl vinylether (23 g, 0.216 mol) was added dropwise to the mixture via the addition funnel. The temperature was then increased to 80° C. and the reaction was held at that temperature for 5 hours. The reaction mixture was then allowed to cool down to room temperature. Thereafter, the reaction mixture was poured into diethyl ether to form three layers: aqueous, ether, and an oil. DI water was used to wash the ether solution 3 times. An oily layer was collected and concentrated to dryness. 12.9 g (61.5%) of bis(4-vinyloxyethyloxyphenyl)phenylsulfonium triflate was obtained. The structure was confirmed using 1H and 19F NMR.

Workup

  1. customA 3-neck-round bottom flask was fitted with a condenser, an addition funnel
  2. temperatureThe temperature was then increased to 80° C.
  3. temperatureto cool down to room temperature
  4. customto form three layers
  5. washto wash the ether solution 3 times
  6. customAn oily layer was collected
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-8976ffb818c24ffabc4a1f4b02079731
Source dataset
uspto-grants-2015_09
Patent number
US09146467B2

Reaction notes

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