Diethyl Ether → 2-(5-Bromo-3-pyridyl)propan-2-ol

HRID 530017

Reaktionsgleichung

Reaktionsgleichung von HRID 530017
[C:1]([C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Br:10])[CH:9]=1)(=[O:3])[CH3:2].[CH3:11][Mg]Br.C(OCC)C>O1CCCC1>[Br:10][C:8]1[CH:9]=[C:4]([C:1]([OH:3])([CH3:11])[CH3:2])[CH:5]=[N:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 8204233-Acetyl-5-bromopyridineHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 223919662-(5-Bromo-3-pyridyl)propan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a cooled (−78° C.) solution of 3-acetyl-5-bromo pyridine (1.98 g, 9.90 mmol) in tetrahydrofuran (33 mL) was added dropwise a solution of methyl magnesium bromide in diethyl ether (3.0 M, 6.60 mL, 19.8 mmol). The reaction was warmed to room temperature, and the resulting mixture was stirred at room temperature overnight. The reaction was then quenched with saturated aqueous ammonium chloride solution and extracted with diethyl ether. The organic extracts were combined, washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by flash chromatography on silica gel (0-60% ethyl acetate in hexanes) provided the title compound: LCMS m/z 217.83 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.61 (s, 1 H), 8.53 (s, 1 H), 8.01 (d, J=1.9 Hz, 1 H), 2.38 (br s, 1 H), 1.61 (6 H).

Aufarbeitung

  1. customThe reaction was then quenched with saturated aqueous ammonium chloride solution
  2. extractionextracted with diethyl ether
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography on silica gel (0-60% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-9d68144ca2c048fe9759be13c9ba3edc
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09351973B2

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