Sodium hydride → (2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)acetonitrile

HRID 887761Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 887761
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[CH3:14][N:15]1[CH:23]=[C:22]2[C:17]([CH:18]=[CH:19][C:20]3[CH2:26][CH2:25][C:24](=O)[C:21]=32)=[N:16]1>O1CCCC1.O>[CH3:14][N:15]1[CH:23]=[C:22]2[C:17]([CH:18]=[CH:19][C:20]3[CH2:26][CH2:25][C:24](=[CH:5][C:3]#[N:4])[C:21]=32)=[N:16]1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 591459262-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-one

Produkt 1

HCID 68699579(2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)acetonitrileAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of 60% sodium hydride (116 mg, 2.90 mmol) in tetrahydrofuran (8 mL) was added diethyl cyanomethylphosphonate (516 μL, 3.19 mmol), and the mixture was stirred at room temperature for 30 min. A solution of 2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-one (180 mg, 0.97 mmol) in tetrahydrofuran (2 mL) was added thereto, and the mixture was stirred at 50° C. for 30 min. The reaction solution was diluted with water, extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=35/65→70/30) to give the title compound (138 mg, yield 68%).

Aufarbeitung

  1. stirringthe mixture was stirred at 50° C. for 30 min
  2. extractionextracted with ethyl acetate
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=35/65→70/30)

Quellen und Nachweise

ORD-Eintrag
ord-d2e72fb199db4e8590cf0c345527a6e8
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247429B2

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