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Water → HCID 86703315, Verbindung

HRID 2409998
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2409998
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].CC(C)([O-])C.[K+].[CH:18]([C:20]1[N:25]=[C:24]([CH2:26][C:27]2[C:35]3[C:30](=[CH:31][C:32]([O:36][CH3:37])=[CH:33][CH:34]=3)[N:29]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:28]=2[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:23]=[CH:22][CH:21]=1)=O.O>CS(C)=O.[Cl-].[Na+].O>[C:1](/[CH:3]=[CH:18]/[C:20]1[N:25]=[C:24]([CH2:26][C:27]2[C:35]3[C:30](=[CH:31][C:32]([O:36][CH3:37])=[CH:33][CH:34]=3)[N:29]([C:38]([O:40][C:41]([CH3:42])([CH3:44])[CH3:43])=[O:39])[C:28]=2[C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)[CH:23]=[CH:22][CH:21]=1)#[N:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 75676Diethyl (cyanomethyl)phosphonateHCID 23665647Potassium tert-butoxideHCID 86703314HCID 86703314, Verbindung

Produkt 1

HCID 86703315HCID 86703315, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679
Dimethyl Sulfoxide
Lösungsmittel
2×
HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of diethyl cyanomethylphosphonate (0.173 mL) in dimethylsulfoxide (6 mL) was added potassium tert-butoxide (127 mg) at room temperature, and the mixture was stirred for 30 minutes. Then a solution of tert-butyl 3-(6-formylpyridin-2-ylmethyl)-6-methoxy-2-phenyl-1H-indole-1-carboxylate (385 mg) in dimethylsulfoxide (3 mL) was added dropwise at room temperature, and the mixture was stirred overnight. To the reaction mixture were added water and saturated brine, followed by extraction with ethyl acetate. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (192 mg). 1H-NMR (CDCl3) δ ppm: 1.23 (9H, s), 3.89 (3H, s), 4.04 (2H, s), 6.55 (1H, d, J=15.8 Hz), 6.82-6.90 (1H, m), 6.96-7.03 (1H, m), 7.04-7.12 (1H, m), 7.23-7.46 (7H, m), 7.48-7.57 (1H, m), 7.82-7.90 (1H, m).

Aufarbeitung

  1. stirringthe mixture was stirred overnight
  2. extractionfollowed by extraction with ethyl acetate
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with water and saturated brine successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-0a31f11f335e4c73ac0279e0ff255656
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08815903B2

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