Pyridine → 2,2,3,3,3-Pentafluoropropyl p-Toluenesulfonate

HRID 733287

Reaktionsgleichung

Reaktionsgleichung von HRID 733287
[F:1][C:2]([F:9])([C:5]([F:8])([F:7])[F:6])[CH2:3][OH:4].N1C=CC=CC=1.[S:16](Cl)([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17].C([O-])([O-])=O.[K+].[K+]>C(Cl)(Cl)Cl>[S:16]([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)([O:4][CH2:3][C:2]([F:9])([F:1])[C:5]([F:8])([F:7])[F:6])(=[O:18])=[O:17]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 98722,2,3,3,3-PentafluoropropanolHCID 11430Potassium Carbonate

Produkt 1

HCID 27760172,2,3,3,3-Pentafluoropropyl p-ToluenesulfonateAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of 2,2,3,3,3-pentafluoropropanol (5.0 mL, 50 mmol) and pyridine (8.1 mL, 100 mmol) in chloroform (100 mL), cooled at 0° C. and under argon, tosyl chloride (14.29 g, 75 mmol) was slowly added. The resulting mixture was allowed to warm up to room temperature and was stirred at this temperature overnight. Then, 10% aqueous K2CO3 solution was added and the mixture was vigorously stirred for 30 min. The layers were separated, and the organic layer was treated again with K2CO3. After that, it was washed with 2 N HCl, dried over Na2SO4 and the solvent was removed, yielding 12.72 g of the desired compound (84% yield).

Aufarbeitung

  1. stirringthe mixture was vigorously stirred for 30 min
  2. customThe layers were separated
  3. additionthe organic layer was treated again with K2CO3
  4. washAfter that, it was washed with 2 N HCl
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-cca5ac87c6764be8ab6a7016fb72dc67
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07589125B2

Verknüpfte Notizen

Wird geladen…