Iodoethane → 4-Chloro-2-propylpyridine

HRID 2099126

Reaktionsgleichung

Reaktionsgleichung von HRID 2099126
[Li+].[CH3:2][CH:3]([N-]C(C)C)C.[Cl:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([CH3:16])[CH:11]=1.ICC>C1COCC1.[Cl-].[Na+].O>[Cl:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([CH2:16][CH2:2][CH3:3])[CH:11]=1

Komponenten

6

Edukt 3

HCID 6340IodoethaneHCID 5813924-Chloro-2-methylpyridineHCID 2724682Lithium diisopropylamide

Produkt 1

HCID 30226654-Chloro-2-propylpyridineAusbeute 67,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
-60 °C

Versuchsvorschrift

To a solution of LDA (0.13 moles) in THF/hexanes (40 mL/40 mL) at −60° C. under argon was added a solution of 4-chloro-2-picoline (15 g) in THF (250 mL) over 20 min. After a further 30 min at −60° C. iodoethane (10.4 mL) in THF (60 mL) was added over 20 min, the reaction stirred at −60° C. for 1.5 h and then allowed to warm to −30° C. The mixture was poured into brine and extracted with dichloromethane. After drying (MgSO4) and purification by chromatography eluting with dichloromethane in petroleum ether (70-100%) followed by dichloromethane containing methanol (0 to 5%) the title compound was obtained as a brown oil (12.35 g). 1H NMR δ (CDCl3) 0.97 (3H, t), 1.75 (2H, m), 2.75 (2H, t), 7.12 (1H, m), 7.16 (1H, d), 8.42 (1H, d).

Aufarbeitung

  1. temperatureto warm to −30° C
  2. extractionextracted with dichloromethane
  3. customAfter drying
  4. custom(MgSO4) and purification by chromatography
  5. washeluting with dichloromethane in petroleum ether (70-100%)
  6. additioncontaining methanol (0 to 5%) the title compound

Quellen und Nachweise

ORD-Eintrag
ord-04399dbe681e422ca08db111e08e91cc
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07569550B2

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