Iodoethane → 2-(2,5-Dimethyl-pyrrol-1-yl)-6-propyl-pyridine

HRID 2358531Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2358531
[CH3:1][C:2]1[N:3]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[Li+].[CH3:16][CH:17]([N-]C(C)C)C.C(I)C>C1COCC1>[CH3:7][C:4]1[N:3]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH2:16][CH3:17])[N:9]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 7931562-(2,5-Dimethyl-1H-pyrrol-1-yl)-6-methylpyridineHCID 2724682Lithium diisopropylamide

Produkt 1

HCID 542277792-(2,5-Dimethyl-pyrrol-1-yl)-6-propyl-pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

A solution of the product from Example 2a (7.53 g, 40.0 mmol) in 30 mL of dry THF was added dropwise with stirring to a solution of LDA (42.4 mmol) in 30 mL of dry THF at −30° C. Stirred at −30° C. for 30 min. Added EtI (3.42 mL, 42.0 mmol) in 20 mL of dry THF dropwise with stirring for 30 min then warmed to room temperature. After 2 h quenched by pouring into saturated NaCl solution and extracted with ether. Dried over MgSO4, filtered and concentrated under vacuum giving the title compound. The product was purified by silica gel column chromatography eluting with EtOAc/hexane to give the title compound (5.21 g, 60%).

Aufarbeitung

  1. temperaturethen warmed to room temperature
  2. customAfter 2 h quenched
  3. additionby pouring into saturated NaCl solution
  4. extractionextracted with ether
  5. dry with materialDried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b8abbd1f918c4f128cd0f1c036af5723
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07763731B2

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