Cesium carbonate → 2-(2-Iodo-6-methylpyridin-3-yloxy)ethanol

HRID 1913431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1913431
[I:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:17][CH2:18][OH:19]>CN(C=O)C>[I:1][C:2]1[C:7]([O:8][CH2:17][CH2:18][OH:19])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 108982-BromoethanolHCID 899572-Iodo-6-methylpyridin-3-ol

Produkt 1

HCID 218737982-(2-Iodo-6-methylpyridin-3-yloxy)ethanolAusbeute 100,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a stirred mixture of 2-iodo-6-methylpyridin-3-ol (530 g, 2.25 mol), Cs2CO3 (876 g, 2.7 mol) and DMF (2.5 L) was added 2-bromo-ethanol (560 g, 4.51 mol) dropwise at 0° C. The mixture was stirred at 90° C. overnight. The reaction was cooled and the solvent was removed in vacuo. The residue was diluted with water (2 L) and the aqueous solution was extracted with CH2Cl2 (3×350 mL). The combined organic layers were washed with brine (2×150 mL), dried over anhydrous Na2SO4 and concentrated to afford 2-(2-iodo-6-methylpyridin-3-yloxy)ethanol (630 g) as a brown solid which was used directly in the next step without further purification.

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. customthe solvent was removed in vacuo
  3. additionThe residue was diluted with water (2 L)
  4. extractionthe aqueous solution was extracted with CH2Cl2 (3×350 mL)
  5. washThe combined organic layers were washed with brine (2×150 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8afbd1aca60b483abc8ac90904fff18f
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609680B2

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