Sodium hydride → [2-(4-Phenylbutyl)-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-ylidene]acetonitrile

HRID 340675Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 340675
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[C:14]1([CH2:20][CH2:21][CH2:22][CH2:23][C:24]2[O:25][C:26]3[C:35]4[C:34](=O)[CH2:33][CH2:32][C:31]=4[CH:30]=[CH:29][C:27]=3[N:28]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[NH4+]>O1CCCC1>[C:14]1([CH2:20][CH2:21][CH2:22][CH2:23][C:24]2[O:25][C:26]3[C:35]4[C:34](=[CH:5][C:3]#[N:4])[CH2:33][CH2:32][C:31]=4[CH:30]=[CH:29][C:27]=3[N:28]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 577812092-(4-Phenylbutyl)-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-one

Produkt 1

HCID 67355173[2-(4-Phenylbutyl)-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-ylidene]acetonitrileAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of 60% sodium hydride (19.5 mg, 0.487 mmol) in tetrahydrofuran (2 mL) was added diethyl cyanomethylphosphonate (85.4 μL, 0.528 mmol) under ice-cooling, and the mixture was stirred for 15 min. Thereto was added a solution of 2-(4-phenylbutyl)-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-one (124 mg, 0.406 mmol) in tetrahydrofuran (2 mL), and the mixture was further stirred for 30 min. To the reaction mixture was added 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. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60) to give the title compound (125 mg, yield 94%).

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was further stirred for 30 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60)

Quellen und Nachweise

ORD-Eintrag
ord-7496d5d480b14974a14bbd764914fc2c
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895591B2

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