Acetone → 2-(6-Bromo-5-methoxypyridin-2-yl)propan-2-ol

HRID 604225

Reaktionsgleichung

Reaktionsgleichung von HRID 604225
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4](I)[N:3]=1.C([Li])CCC.[CH3:16][C:17]([CH3:19])=[O:18].O>C1(C)C=CC=CC=1.CCCCCC.C(OCC)(=O)C>[Br:1][C:2]1[N:3]=[C:4]([C:17]([OH:18])([CH3:19])[CH3:16])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Komponenten

8

Edukt 4

HCID 180AcetoneHCID 962WaterHCID 110990402-Bromo-6-iodo-3-methoxypyridineHCID 178418339Butyllithium

Produkt 1

HCID 575560732-(6-Bromo-5-methoxypyridin-2-yl)propan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-Bromo-6-iodo-3-methoxy-pyridine (500 mg) is dissolved in dry toluene (5 ml) and thereto is added dropwise 1.6M n-butyllithium in hexane (1 ml) at −78° C. under nitrogen atmosphere, and the mixture is stirred for 1 hour and thereto is added acetone (0.23 ml), and the mixture is stirred overnight. To the reaction solution are added water and ethyl acetate, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=4:1→3:2) to give 2-(6-bromo-5-methoxy-pyridin-2-yl)-propan-2-ol (197 mg). MS (m/z): 246/248 [M+H]+

Aufarbeitung

  1. stirringthe mixture is stirred overnight
  2. customthe mixture is separated
  3. washthe organic layer is washed with a saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=4:1→3:2)

Quellen und Nachweise

ORD-Eintrag
ord-35509863473d45fe99c21d5771979cff
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906517B2

Verknüpfte Notizen

Wird geladen…