Hexane → HCID 18673776, Verbindung

HRID 2299034Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2299034
C([Li])CCC.CCCCCC.Br[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][CH3:21])[N:14]=1.[CH2:22]([Sn:26](Cl)([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH3:25]>CCOCC>[CH2:20]([O:19][C:15]1[N:14]=[C:13]([Sn:26]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:22][CH2:23][CH2:24][CH3:25])[CH:18]=[CH:17][CH:16]=1)[CH3:21]

Komponenten

6

Edukt 4

HCID 8058HexaneHCID 15096Tributyltin ChlorideHCID 12010182-Bromo-6-ethoxypyridineHCID 178418339Butyllithium

Produkt 1

HCID 18673776HCID 18673776, VerbindungAusbeute 34,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A 2.5M solution of n-butyllithium in hexane (4.5 ml, 11.3 mmol) was added to a stirred solution of 2-bromo-6-ethoxypyridine (Rec. Trav. chim., 1965, 84, 53; 2.1 g, 11.3 mmol) in anhydrous ether (25 ml), under nitrogen, at about −40° C. After about 20 minutes, tri-n-butyltin chloride (3.1 ml, 11.4 mmol) was slowly added and, after a further 15 minutes, the reaction mixture was allowed to warm to room temperature. The resulting mixture was quenched by the addition of aqueous ammonium chloride solution, then the organic phase separated, washed with water, dried (MgSO4) and evaporated under reduced pressure. The residue was purified by flash chromatography, using an elution gradient of pentane:dichloromethane (100:0 to 80:20), to give the title compound (1.6 g, 34%) as a colourless oil. δ(CDCl3): 0.90 (t,9H), 1.08 (t,6H), 1.30-1.42 (m,9H), 1.58 (m,6H), 4.40 (q,2H), 6.53 (d,1H), 6.97 (d,1H), 7.39 (dd,1H).

Aufarbeitung

  1. customThe resulting mixture was quenched by the addition of aqueous ammonium chloride solution
  2. customthe organic phase separated
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-10064a0595f443ea92d1f483a742133a
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06495568B1

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