6-Bromopyridine-2-carbaldehyde → 1-(6-Bromo-2-pyridinyl)ethanol

HRID 460198Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 460198
[Br:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH3:10][Mg]I>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]([CH:8]([OH:9])[CH3:10])[CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 27570096-Bromopyridine-2-carbaldehydeHCID 178418373HCID 178418373, Verbindung

Produkt 1

HCID 110634791-(6-Bromo-2-pyridinyl)ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

6-Bromo-2-pyridine carboxaldehyde (1.0 g, 5.37 mmol) in dry THF (20 mL) was cooled to −78° C. followed by adding MeMgI (2.0 mL, 5.91 mmol) dropwise via the addition funnel. The cooling bath was removed. The resulting mixture was stirred for 1 h then quenched with sat. NH4Cl. Solvent was removed. The residue was partitioned between water and CHCl3. The organic layer was washed with H2O, brine, dried over MgSO4. Solvent was removed and crude compound was purified by chromatography on silica gel. Elution with hexane:acetone mixture (70:30) gave a white solid. MS m/z: 201.9(M+H). Calc'd. for C7H8BrNO-200.98.

Aufarbeitung

  1. customThe cooling bath was removed
  2. customthen quenched with sat. NH4Cl
  3. customSolvent was removed
  4. customThe residue was partitioned between water and CHCl3
  5. washThe organic layer was washed with H2O, brine
  6. dry with materialdried over MgSO4
  7. customSolvent was removed
  8. customcrude compound was purified by chromatography on silica gel
  9. washElution with hexane
  10. customacetone mixture (70:30) gave a white solid

Quellen und Nachweise

ORD-Eintrag
ord-a10fa372cfd54433be8a370844bcf3dd
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07196104B2

Notizen zur Reaktion

Wird geladen…