Tetramethylene sulfoxide → 4-(2,2,2-Trifluoroethoxy)-1-naphthyl-tetrahydrothiophenium 2-benzoyloxy-1,1,3,3,3-pentafluoro-propane-1-sulfonate

HRID 1907085

Reaktionsgleichung

Reaktionsgleichung von HRID 1907085
[F:1][C:2]([F:16])([F:15])[CH2:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1.[CH2:17]1[S:21](=O)[CH2:20][CH2:19][CH2:18]1.C(OC(C)C)(C)C.[C:30]([O:38][CH:39]([C:47]([F:50])([F:49])[F:48])[C:40]([F:46])([F:45])[S:41]([O-:44])(=[O:43])=[O:42])(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[Na+]>CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.O>[C:30]([O:38][CH:39]([C:47]([F:49])([F:50])[F:48])[C:40]([F:45])([F:46])[S:41]([O-:44])(=[O:43])=[O:42])(=[O:37])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1.[F:1][C:2]([F:15])([F:16])[CH2:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([S+:21]2[CH2:17][CH2:18][CH2:19][CH2:20]2)=[CH:7][CH:6]=1

Komponenten

7

Edukt 4

HCID 1128Tetramethylene sulfoxideHCID 7914Diisopropyl EtherHCID 13443056HCID 13443056, VerbindungHCID 58112889Sodium 2-benzoyloxy-1,1,3,3,3-pentafluoropropanesulfonate

Produkt 1

HCID 866642974-(2,2,2-Trifluoroethoxy)-1-naphthyl-tetrahydrothiophenium 2-benzoyloxy-1,1,3,3,3-pentafluoro-propane-1-sulfonateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 86584057Phosphorus Pentoxide-Methanesulfonic AcidLösungsmittel

Versuchsvorschrift

In 6 g of Eaton's reagent (Aldrich, diphosphorus pentoxide/methanesulfonic acid solution) was dispersed 2.4 g (0.0107 mol) of 1-(2,2,2-trifluoroethoxy)naphthalene in Synthesis Example 1-3. With stirring, 2.2 g (0.0214 mol) of tetramethylene sulfoxide was added dropwise to the dispersion. The solution was matured overnight at room temperature and combined with 30 g of water and 30 g of diisopropyl ether, from which a water layer was separated. The water layer was again washed with 30 g of diisopropyl ether. This aqueous solution was combined with 3.4 g (0.0095 mol) of sodium 2-benzoyloxy-1,1,3,3,3-pentafluoropropanesulfonate synthesized in accordance with the teaching of JP-A 2007-145797, after which extraction was effected twice with 50 g of dichloromethane. The organic layer was washed with water and distilled in vacuum to remove the solvent. The residue was poured into isopropyl ether for crystallization, filtered and dried, obtaining the target compound. White crystals, 5.3 g, yield 87%.

Aufarbeitung

  1. customin Synthesis Example 1-3
  2. customwas separated
  3. washThe water layer was again washed with 30 g of diisopropyl ether
  4. customsynthesized in accordance with the teaching of JP-A 2007-145797
  5. extractionafter which extraction
  6. washThe organic layer was washed with water
  7. distillationdistilled in vacuum
  8. customto remove the solvent
  9. additionThe residue was poured into isopropyl ether for crystallization
  10. filtrationfiltered
  11. customdried
  12. customobtaining the target compound

Quellen und Nachweise

ORD-Eintrag
ord-0e40b955ab584c718cf2f0d8aaaec49c
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08597869B2

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