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Potassium Iodide → HCID 57426205, Verbindung

HRID 551047
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 551047
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]([CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:7][NH:8]2)([O-:3])=[O:2].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].Br[CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32]>CC(C)=O>[C:34]([O:33][C:31](=[O:32])[CH2:30][N:8]1[C:9]2[C:5](=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[CH:11][CH:10]=2)[CH:6]([CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:7]1)([CH3:37])([CH3:36])[CH3:35]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 79177tert-Butyl bromoacetateHCID 57426204HCID 57426204, Verbindung

Produkt 1

HCID 57426205HCID 57426205, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180
Acetone
Lösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-(4-nitro-2,3-dihydro-1H-indol-3-yl)butanoate from Step B (1.10 g, 3.95 mmol), sodium carbonate (628 mg, 5.93 mmol), and potassium iodide (131 mg, 0.79 mmol) in acetone (10 mL) was added tert-butyl bromoacetate (17.5 mL, 119 mmol). The mixture was heated at reflux for 18 h, then cooled to ambient temperature and concentrated in vacuo. The residue was partitioned between H2O (30 mL) and EtOAc (2×60 mL) and the organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—90:10 to 65:35, to give the title compound. MS: m/z=365 (M+1).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 h
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between H2O (30 mL) and EtOAc (2×60 mL)
  5. dry with materialthe organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with a gradient of hexane

Quellen und Nachweise

ORD-Eintrag
ord-e82dd178f4484755937cde8c839fbff3
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07947677B2

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