Water → 2-Hydroxy-2-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl 4-methylbenzenesulfonate

HRID 623477Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 623477
[F:1][C:2]([F:16])([F:15])[CH2:3][O:4][C:5]1[N:10]=[CH:9][C:8]([CH:11]([OH:14])[CH2:12][OH:13])=[CH:7][CH:6]=1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.N1C=CC=CC=1.O>ClCCl>[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([O:13][CH2:12][CH:11]([OH:14])[C:8]2[CH:9]=[N:10][C:5]([O:4][CH2:3][C:2]([F:1])([F:15])[F:16])=[CH:6][CH:7]=2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 73974-Toluenesulfonyl chloride2×HCID 675099191-(6-(2,2,2-Trifluoroethoxy)pyridin-3-yl)ethane-1,2-diol

Produkt 1

HCID 874265272-Hydroxy-2-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl 4-methylbenzenesulfonateAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethane-1,2-diol (1.01 g, 4.24 mmol, Step-3, single enantiomer), p-toluenesulfonyl chloride (0.97 g, 5.09 mmol) and pyridine (3.43 mL, 42.4 mmol) in dichloromethane (21 mL) is stirred at room temperature for 20 hours. Then p-toluenesulfonyl chloride (0.97 g, 5.09 mmol) is added to the reaction mixture and stirred for 24 hours. The reaction mixture is poured into water and extracted with ethyl acetate and dried over sodium sulfate and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (2:1 to 1:1) to give 1.64 g (99% yield) of the title compound as colorless oil.

Aufarbeitung

  1. stirringstirred for 24 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (2:1 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-61a3584e0640493f88955f8f6e0168da
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09302991B2

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