Diglyme → HCID 131726624, compound

HRID 492274Notes

Reaction equation

HRID 492274 reaction equation
[CH2:1]=[C:2]([C:10]([O:13]S(F)(=O)=O)([F:12])[F:11])[C:3]([C:6]([F:9])([F:8])[F:7])([F:5])[F:4].[F-:18].[K+].[F:20][C:21]([F:29])([F:28])[C:22]([C:24]([F:27])([F:26])[F:25])=O.COCCOCCOC>O>[CH2:1]=[C:2]([C:10]([O:13][C:22]([C:24]([F:27])([F:26])[F:25])([C:21]([F:29])([F:28])[F:20])[F:18])([F:12])[F:11])[C:3]([C:6]([F:9])([F:8])[F:7])([F:5])[F:4]

Participants

6

Reactant 4

HCID 8150DiglymeHCID 12695HexafluoroacetoneHCID 522689Potassium FluorideHCID 85887655HCID 85887655, compound

Product 1

HCID 131726624HCID 131726624, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

CH2═C(CF2CF3)CF2OSO2F (5 g, 17 mmole) is added at 20° C. to (CF3)2CCFOK, prepared at 10° C. from freshly dried KF (3 g, 17.2 mmole), hexafluoroacetone (HFA) (3 g, 18 mmole) and dry diglyme (15 ml). The reaction mixture is agitated for 1 hour at 20° C. and then poured into water, the organic layer separating. The organic layer is washed with aqueous sodium bicarbonate solution, then water, after which it is dried over (MgSO4). Distillation of the reaction mixture gives CH2═C(CF2CF3)CF2OCF(CF3)2 (4 g, 62% yield, b.pt. 118-120° C.). This example demonstrates that the fluorosulfates of the higher homolog of hexafluoroisobutylene react with nucleophiles under the same mild conditions that characterize the reactions of CH2═C(CF3)CF2OSO2F.

Workup

  1. customthe organic layer separating
  2. washThe organic layer is washed with aqueous sodium bicarbonate solution
  3. dry with materialwater, after which it is dried over (MgSO4)
  4. distillationDistillation of the reaction mixture

Sources & evidence

ORD record
ord-a96bab604f3249528184ad4ffebf3536
Source dataset
uspto-grants-2009_05
Patent number
US07531689B2

Reaction notes

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