Ethyl Acetate → 4-Tert-butyl-2-chloro-6-methylpyridine

HRID 1446719Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1446719
P(Cl)(Cl)([Cl:3])=O.[C:6]([C:10]1[CH:15]=[CH:14][N+:13]([O-])=[C:12]([CH3:17])[CH:11]=1)([CH3:9])([CH3:8])[CH3:7].C(OCC)(=O)C>ClCCl>[Cl:3][C:14]1[CH:15]=[C:10]([C:6]([CH3:9])([CH3:8])[CH3:7])[CH:11]=[C:12]([CH3:17])[N:13]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 24813Phosphorus oxychlorideHCID 594853984-tert-Butyl-2-methyl-pyridine 1-oxide

Produkt 1

HCID 601265994-Tert-butyl-2-chloro-6-methylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Add phosphorus oxychloride (15 mL) to 4-tert-butyl-2-methyl-pyridine 1-oxide (2.00 g, 12.10 mmol) and heat to 100° C. for 36 hours. Evaporate off the excess phosphorus oxychloride. Treat the oil cautiously with ice and water with stirring and make basic by treatment with aqueous bicarbonate solution. Extract with dichloromethane (3×75 mL) and pool, desiccate, filter, and concentrated. Chromatograph the crude product on silica using a gradient of (0→5→8%) ethyl acetate in dichloromethane to afford the title compound (0.82 g, 4.46 mmol). MS (ESI), m/z 184 (M+1).

Aufarbeitung

  1. customEvaporate off the excess phosphorus oxychloride
  2. additionTreat the oil cautiously with ice and water
  3. extractionExtract with dichloromethane (3×75 mL) and pool, desiccate
  4. filtrationfilter
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2d263cae928d4b339bb7ec3c197b9b7c
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666879B2

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