Imidazole → 3-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloropyridine

HRID 1686074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1686074
[Cl:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[CH:4][N:3]=1.N1C=CN=C1.[CH3:15][C:16]([Si:19](Cl)([CH3:21])[CH3:20])([CH3:18])[CH3:17]>C(Cl)Cl>[Si:19]([O:9][CH2:8][C:7]1[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][CH:6]=1)([C:16]([CH3:18])([CH3:17])[CH3:15])([CH3:21])[CH3:20]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 2763647(2-Chloropyridin-3-yl)methanol

Produkt 1

HCID 183681113-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloropyridineAusbeute 85,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-3-pyridylmethanol (2.07 g) in 100 mL CH2Cl2 was added imidazole (1.96 g). TBDMSCl (2.39 g) was added in one portion, and the reaction was stirred at room temperature for 23 h, then filtered through a fritted funnel The liquid filtrate was concentrated and purified via flash chromatography to give 3.18 g of 3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloropyridine.

Aufarbeitung

  1. filtrationfiltered through a fritted funnel The liquid filtrate
  2. concentrationwas concentrated
  3. custompurified via flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9f811164215d47569c064d224fc3e95b
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148535B2

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