HCID 11197766, Verbindung → HCID 67354173, Verbindung

HRID 1846150Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1846150
[CH3:1][C:2]1[N:3]([C:8]2[CH:13]=[C:12]([CH3:14])[C:11]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:10]([CH3:23])[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[Li]C1C=CC=CC=1.Br[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C1COCC1.CCCCCC>[CH3:1][C:2]1[N:3]([C:8]2[CH:13]=[C:12]([CH3:14])[C:11]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:10]([CH2:23][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][O:41][CH2:42][C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1

Komponenten

6

Edukt 3

HCID 11197766HCID 11197766, VerbindungHCID 67355477HCID 67355477, VerbindungHCID 178506676HCID 178506676, Verbindung

Produkt 1

HCID 67354173HCID 67354173, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a stirred solution at −78° C. containing 1.42 g (4.63 mmol) of 2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-benzyloxy-4,6-dimethylpyridine (16) in 20 mL of anhydrous THF were added 5.15 mL (9.27 mmol) of a 1.8 M solution of PhLi in hexane followed by 1.45 g (4.63 mmol) of 9-bromo-1-(benzyloxy)nonane (1). The reaction mixture was stirred under argon atmosphere at −78° C. for 30 min. then the reaction mixture was warmed to room temperature slowly, and the reaction mixture was stirred 30 min. The reaction was quenched with saturated aqueous NaHCO3 and the poured into 150 mL of water. The mixture was then extracted with two portions of 150 mL of ethyl acetate. The combined organic solution was then washed with a portion of 100 mL of brine, dried (MgSO4) and then concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column. Elution with hexanes-ethyl acetate 4:1 gave the expected product as light yellow oil: yield 1.22 g (49%) 1H-NMR (CDCl3) δ 7.54-7.37 (m, 10H), 6.93, (s, 1H), 5.94 (s, 2H), 4.95 (s, 2H), 4.55 (s, 2H), 3.52 (t, 2H, J=6.4), 2.91 (t, 2H, J=8.0) 2.39 (s, 3H), 2.51 (s, 6H), 1.82 (m, 2H), 1.65 (m, 2H), 1.33 (m, 12H); 13C-NMR (CDCl3) δ 155.94, 150.86, 146.89, 142.59, 138.80, 136.92, 128.69, 128.49, 128.38, 127.81, 127.65, 127.49, 121.75, 106.55, 75.30, 72.89, 70.55, 32.21, 29.85, 29.68, 29.63, 29.60, 29.59, 29.57, 29.53, 28.99, 26.27, 16.42, 13.30.

Aufarbeitung

  1. temperaturethe reaction mixture was warmed to room temperature slowly
  2. stirringthe reaction mixture was stirred 30 min
  3. customThe reaction was quenched with saturated aqueous NaHCO3
  4. additionthe poured into 150 mL of water
  5. extractionThe mixture was then extracted with two portions of 150 mL of ethyl acetate
  6. washThe combined organic solution was then washed with a portion of 100 mL of brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under diminished pressure
  9. customThe residue was purified by chromatography on a silica gel column
  10. washElution with hexanes-ethyl acetate 4:1

Quellen und Nachweise

ORD-Eintrag
ord-05fda82611704499800ec6848538a95c
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952025B2

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