Sodium hydride → 1-[(6-Methoxypyridin-3-yl)sulfonyl]-5-phenyl-1H-pyrrole-3-carbaldehyde

HRID 1012411

Reaktionsgleichung

Reaktionsgleichung von HRID 1012411
[C:1]1([C:7]2[NH:11][CH:10]=[C:9]([CH:12]=[O:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].C1OCCOCCOCCOCCOC1.[CH3:31][O:32][C:33]1[N:38]=[CH:37][C:36]([S:39](Cl)(=[O:41])=[O:40])=[CH:35][CH:34]=1>O1CCCC1.C(OCC)(=O)C>[CH3:31][O:32][C:33]1[N:38]=[CH:37][C:36]([S:39]([N:11]2[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:8][C:9]([CH:12]=[O:13])=[CH:10]2)(=[O:41])=[O:40])=[CH:35][CH:34]=1

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 110520905-Phenyl-1H-pyrrole-3-carboxaldehydeHCID 223447096-Methoxypyridine-3-sulfonyl chloride

Produkt 1

HCID 866207551-[(6-Methoxypyridin-3-yl)sulfonyl]-5-phenyl-1H-pyrrole-3-carbaldehydeAusbeute 17,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Under an argon atmosphere, 5-phenyl-1H-pyrrole-3-carbaldehyde (171 mg) was dissolved in absolute tetrahydrofuran (20 mL), and sodium hydride (60% in oil, 200 mg) was added at room temperature while stirring. After stirring at the same temperature for 15 min, 15-crown-5 (1.01 mL) was added, and the mixture was further stirred at the same temperature for 15 min. 6-Methoxypyridin-3-ylsulfonyl chloride (623 mg) was added, and the mixture was stirred at the same temperature for 1 hr. The reaction mixture was diluted with ethyl acetate, washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=19:1→1:1) to give the title compound as an oil (yield 59 mg, 17%).

Aufarbeitung

  1. stirringAfter stirring at the same temperature for 15 min
  2. stirringthe mixture was further stirred at the same temperature for 15 min
  3. stirringthe mixture was stirred at the same temperature for 1 hr
  4. washwashed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=19:1→1:1)

Quellen und Nachweise

ORD-Eintrag
ord-e981f6f16daf4b25b326a55078c4279e
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977488B2

Verknüpfte Notizen

Wird geladen…