2-Pyridinecarboxaldehyde → 2,2,2-Trifluoro-1-(pyridin-2-yl)ethan-1-ol

HRID 1186336Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1186336
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[O:8].[F:9][C:10]([Si](C)(C)C)([F:12])[F:11].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:9][C:10]([F:12])([F:11])[CH:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[OH:8]

Komponenten

5

Edukt 3

HCID 142732-PyridinecarboxaldehydeHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium Fluoride

Produkt 1

HCID 137429262,2,2-Trifluoro-1-(pyridin-2-yl)ethan-1-olAusbeute 126,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

According to Reference Example 8-12, by use of 2-pyridinecarboxaldehyde (500 μL, 5.26 mmol), (trifluoromethyl)trimethylsilane (932 μL, 6.31 mmol), tetrabutylammonium fluoride (a 1.0 mol/L solution in tetrahydrofuran, 526 μL, 0.526 mmol) and tetrahydrofuran (10 mL), the mixture was stirred and reacted at room temperature for 10 minutes. Then, purification by silica gel column chromatography (chloroform/methanol=9/1) was performed to give 2-(2,2,2-trifluoro-1-hydroxyethyl)pyridine (Compound CN) (1.18 g, yield: quantitative).

Aufarbeitung

  1. customreacted at room temperature for 10 minutes
  2. customThen, purification by silica gel column chromatography (chloroform/methanol=9/1)

Quellen und Nachweise

ORD-Eintrag
ord-358ac4f581e94a6c855b75484f4aef9e
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673908B2

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