Tetrahydrofuran → HCID 14618903, compound

HRID 2283154Notes

Reaction equation

HRID 2283154 reaction equation
C1COCC1.[CH:6]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)=[CH2:7].C(=O)([O-])[O-].[K+].[K+].[F:21][C:22]([F:46])([F:45])[C:23]([F:44])([F:43])[C:24]([F:42])([F:41])[O:25][C:26]([F:40])([C:31]([F:39])([F:38])[O:32][C:33]([F:37])=[C:34]([F:36])[F:35])[C:27]([F:30])([F:29])[F:28]>C(O)C(O)C>[F:36][C:34]([F:35])([O:14][C:11]1[CH:12]=[CH:13][C:8]([CH:6]=[CH2:7])=[CH:9][CH:10]=1)[CH:33]([F:37])[O:32][C:31]([F:38])([F:39])[C:26]([F:40])([O:25][C:24]([F:41])([F:42])[C:23]([F:43])([F:44])[C:22]([F:21])([F:45])[F:46])[C:27]([F:30])([F:29])[F:28]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 624534-VinylphenolHCID 1026621,1,1,2,3,3-Hexafluoro-2-(heptafluoropropoxy)-3-((trifluorovinyl)oxy)propane

Product 1

HCID 14618903HCID 14618903, compound

Reagents, catalysts & solvents 1

HCID 1030Propylene GlycolSolvent

Procedure

In the dry box, THF (50 mL) and 4-vinylphenol (5.00 g of a 10% solution in propylene glycol) were added to an oven dry RB flask equipped with a stirrer, Potassium carbonate (0.35 g, 0.0025 mol) was then added. 1,1,1,2,2,3,3-Heptafluoro-3-(1,1,1,2,3,3-hexafluoro-3-(1,2,2-trifluorovinyloxy)propan-2-yloxy)propane (2.70 g, 0.00625 mol) was then added via the addition funnel and the reaction allowed to stir at room temperature. The reaction mixture was heated to a gentle reflux under nitrogen overnight. An aliquot was withdrawn and concentrated under vacuum and analyzed via proton NMR which showed the complete conversion to be 1-(1,1,2-trifluoro-2-(1,1,2,3,3,3-hexafluoro-2-(perfluoropropoxy)propoxy)ethoxy)-4-vinylbenzene. The cooled reaction mixture was then concentrated at reduced pressure taken up in methylene chloride washed with water (˜25 mL) separated, then dried over anhydrous sodium sulfate. The separated organic phase was then concentrated at reduced pressure and then column chromatograph on silica gel obtaining 1.15 g (about 50.0%) of the theoretical yield) of product.

Workup

  1. customdry RB flask
  2. customequipped with a stirrer
  3. temperatureThe reaction mixture was heated to
  4. temperaturea gentle reflux under nitrogen overnight
  5. customAn aliquot was withdrawn
  6. concentrationconcentrated under vacuum
  7. customThe cooled reaction mixture
  8. concentrationwas then concentrated at reduced pressure
  9. washwashed with water (˜25 mL)
  10. customseparated
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationThe separated organic phase was then concentrated at reduced pressure
  13. customcolumn chromatograph on silica gel obtaining 1.15 g (about 50.0%) of the theoretical yield) of product

Sources & evidence

ORD record
ord-1c5b03de38d54a65bc3378c133661f96
Source dataset
uspto-grants-2015_09
Patent number
US09145356B2

Reaction notes

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