Ethanol → 2-(2-ETHOXYPYRIDIN-3-YLOXY)ETHANOL

HRID 493346Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 493346
Br[C:2]1[C:7]([O:8][CH2:9][CH2:10][O:11][Si](C(C)(C)C)(C)C)=[CH:6][CH:5]=[CH:4][N:3]=1.[O-:19][CH2:20][CH3:21].[Na+].CCO>>[CH2:20]([O:19][C:2]1[C:7]([O:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:5]=[CH:4][N:3]=1)[CH3:21]

Komponenten

4

Edukt 3

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 17946394HCID 17946394, Verbindung

Produkt 1

HCID 115138722-(2-ETHOXYPYRIDIN-3-YLOXY)ETHANOLAusbeute 41 %

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

The product obtained in Step 1 above (13.2 g, 39.7 mmol) was added to sodium ethoxide in EtOH [prepared from Na (10.5 g, 457 mmol) and EtOH (200 mL)]. The resulting mixture was heated at 70° C. overnight. After cooling to ambient temperature, the reaction mixture was diluted with ice water (0.8 L) and extracted with EtOAc (×4). The combined organic phases were washed twice with brine, dried (MgSO4) and concentrated. The resulting dark red oil was purified by column chromatography on silica using toluene/Et3N (95:5), followed by (90:10), as eluent to give 3.0 g (41%) of the title product as a red oil. HRMS m/z calcd for C9H13NO3 (M)+ 183.0896. Found: 183.0895.

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature
  2. extractionextracted with EtOAc (×4)
  3. washThe combined organic phases were washed twice with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe resulting dark red oil was purified by column chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-7356ae6e618c450a908dacbeb028d583
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07534794B2

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