Water → 4,4,5,5,5-Pentafluoropentyl 4-methylbenzenesulfonate

HRID 515802Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 515802
[F:1][C:2]([F:11])([C:7]([F:10])([F:9])[F:8])[CH2:3][CH2:4][CH2:5][OH:6].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.C(N(CC)CC)C.O>C(Cl)Cl>[CH3:22][C:12]1[CH:17]=[CH:16][C:15]([S:18]([O:6][CH2:5][CH2:4][CH2:3][C:2]([F:11])([F:1])[C:7]([F:8])([F:9])[F:10])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 5479674,4,5,5,5-Pentafluoropentan-1-ol

Produkt 1

HCID 220330274,4,5,5,5-Pentafluoropentyl 4-methylbenzenesulfonateAusbeute 91,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 4,4,5,5,5-pentafluoropentan-1-ol (1 g, 5.6 mmol), p-toluenesulfonylchloride (1.3 g, 6.8 mmol), and triethylamine (1.2 mL, 8.4 mmol) in DCM (20 mL) was stirred at room temperature for 18 h. Water was added to the reaction mixture, the two layers were separated, and the aqueous layer was extracted with DCM (2×). The organics were combined, dried over sodium sulfate, and evaporated to dryness. The residue was purified by column chromatography on silica gel eluting with 0 to 20% EtOAc/hexanes to afford 1.7 g of 4,4,5,5,5-pentafluoropentyl 4-methylbenzenesulfonate as a colorless oil.

Aufarbeitung

  1. customthe two layers were separated
  2. extractionthe aqueous layer was extracted with DCM (2×)
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. customThe residue was purified by column chromatography on silica gel eluting with 0 to 20% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-45186e51e05b47b7a00aa3bd76654222
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108944B2

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