Diisopropylethylamine → 2-Chloro-6-(2-(trimethylsilanyl)ethoxymethoxymethyl)pyridine

HRID 376281

Reaktionsgleichung

Reaktionsgleichung von HRID 376281
ClCC([Si](C)(C)C)[CH2:4][O:5][CH2:6][CH:7]([Si:10]([CH3:13])([CH3:12])[CH3:11])CCl.[Cl:18][C:19]1[N:24]=[C:23]([CH2:25][OH:26])[CH:22]=[CH:21][CH:20]=1.C(N(C(C)C)CC)(C)C>ClCCl>[Cl:18][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]([CH2:25][O:26][CH2:4][O:5][CH2:6][CH2:7][Si:10]([CH3:11])([CH3:12])[CH3:13])[N:24]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 182139(6-Chloropyridin-2-yl)methanolHCID 57232046HCID 57232046, Verbindung

Produkt 1

HCID 108022522-Chloro-6-(2-(trimethylsilanyl)ethoxymethoxymethyl)pyridineAusbeute 76,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3.20 ml of chloromethyl-2-(trimethylsilyl)ethyl ether (18.2 mmol) are added dropwise to a solution containing 2.50 g of (6-chloropyridin-2-yl)methanol (17.4 mmol), 3.30 ml of diisopropylethylamine (19.1 mmol) and 20 ml of dichloromethane cooled to 0° C. maintained under a nitrogen atmosphere. The mixture is stirred for 3 hours at room temperature and then the dichloromethane is evaporated off, the residue is taken up in water, the mixture is extracted with diethyl ether, the organic phase is washed with water and then dried over sodium sulfate. After filtration and evaporation of the solvent, the title product is isolated by chromatography on a silica column (eluent: dichloromethane).

Aufarbeitung

  1. temperaturemaintained under a nitrogen atmosphere
  2. customthe dichloromethane is evaporated off
  3. extractionthe mixture is extracted with diethyl ether
  4. washthe organic phase is washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration and evaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-33e28e9b139c4391b28bbb1113071079
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06020345

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