Sodium hydride → HCID 59334588, Verbindung

HRID 1639815Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1639815
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[Cl:14][C:15]1[C:23]2[C:19](=[CH:20][N:21]([CH3:24])[N:22]=2)[C:18]([CH:25]=O)=[CH:17][CH:16]=1>O1CCCC1.[Cl-].[NH4+]>[Cl:14][C:15]1[C:23]2[C:19](=[CH:20][N:21]([CH3:24])[N:22]=2)[C:18](/[CH:25]=[CH:3]/[C:1]#[N:2])=[CH:17][CH:16]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 59334563HCID 59334563, Verbindung

Produkt 1

HCID 59334588HCID 59334588, VerbindungAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 25517Ammonium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of diethyl cyanomethylphosphonate (1.62 mL, 10.02 mmol) in tetrahydrofuran (70 mL) was added 60% sodium hydride (370 mg, 9.25 mmol) under ice-cooling, and the mixture was stirred at 0° C. for 30 min. To the mixture was added a solution of 7-chloro-2-methyl-2H-indazole-4-carbaldehyde (1.50 g, 7.71 mmol) in tetrahydrofuran (30 mL) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. The reaction solution was diluted with saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=15/85→40/60) to give the title compound (1.45 g, yield 86%).

Aufarbeitung

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 1 hr
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=15/85→40/60)

Quellen und Nachweise

ORD-Eintrag
ord-f8eec64496ef4aa78d322f36d908b7f9
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110585B2

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