3-Bromo-5-methylpyridine → 1-(5-Methylpyridin-3-yl)ethan-1-one

HRID 595041Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 595041
BrC1[CH:3]=[N:4][CH:5]=C(C)C=1.CON(C)[C:12](=[O:14])[CH3:13].[Li][CH2:17][CH2:18][CH2:19][CH3:20]>C(OCC)C>[CH3:20][C:19]1[CH:18]=[C:17]([C:12](=[O:14])[CH3:13])[CH:5]=[N:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 8177133-Bromo-5-methylpyridineHCID 178502655HCID 178502655, Verbindung

Produkt 1

HCID 5775691-(5-Methylpyridin-3-yl)ethan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To 3-bromo-5-methylpyridine 1-1 (2 g, 11.63 mmol) in diethyl ether (30 ml) at −78° C. was added uLi (8.72 ml, 13.95 mmol) dropwise. After 30 min, N-methoxy-N-methylacetamide n-BuLi was added. The resulting mixture was stirred at −78° C. for 2 h then at rt overnight, quenched with saturated NH4Cl solution and diluted with EtOAc. The organic layer was washed with water, brine, dried over magnesium sulfate and concentrated to give a yellow residue, which was purified by column chromatography (0-65% EtOAc in hexane) to give the desired product 1-2: 1H NMR (400 MHz, CDCl3) δ 8.98 (s, 1H), 8.62 (s, 1H), 8.04 (s, 1H), 2.63 (s, 3H), 2.41 (s, 3H).

Aufarbeitung

  1. customat rt overnight, quenched with saturated NH4Cl solution
  2. additiondiluted with EtOAc
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto give a yellow residue, which
  7. customwas purified by column chromatography (0-65% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-b7d8f71043c243d7a29a2a1562dd9f14
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242995B2

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