2,6-Dibromopyridine → 2-Bromo-6-[(oxolan-3-yl)oxy]pyridine

HRID 479666Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 479666
[OH:1][C@H:2]1[CH2:6][CH2:5][O:4][CH2:3]1.[H-].[Na+].[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12](Br)[N:11]=1>C1COCC1>[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:1][CH:2]2[CH2:6][CH2:5][O:4][CH2:3]2)[N:11]=1

Komponenten

5

Edukt 3

HCID 122742,6-DibromopyridineHCID 24758Sodium hydrideHCID 2733227(S)-(+)-3-Hydroxytetrahydrofuran

Produkt 1

HCID 187717992-Bromo-6-[(oxolan-3-yl)oxy]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (S)-(+)-3-hydroxy-tetrahydrofuran (0.34 mL, 4.2 mmol) and dry THF (20 mL) was added NaH (0.17 g, 4.2 mmol, 60%) under N2 at RT. After 5 min, added 2,6-dibromopyridine. Stirred at RT for 4 h. Quenched with H2O and extracted with EtOAc. Washed organic layer with saturated NH4Cl, brine, dried (MgSO4) and concentrated in vacuo to give 2-bromo-6-(tetrahydro-furan-3-yloxy)-pyridine as a clear, colorless oil. MS m/z: 245.2 (M+H). Calc'd for C9H10BrNO2—244.09.

Aufarbeitung

  1. customQuenched with H2O
  2. extractionextracted with EtOAc
  3. dry with materialWashed organic layer with saturated NH4Cl, brine, dried (MgSO4)
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-04d41223e81340bd815c31a8a3884132
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06645990B2

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