Boron trifluoride etherate → 2-(5-Phenyloxazol-2-yl)acetonitrile

HRID 1397370Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1397370
B(F)(F)F.CCOCC.[C:10](#[N:14])[CH2:11][C:12]#[N:13].[N+](=[CH:17][C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:19])=[N-]>C(Cl)Cl>[C:20]1([C:18]2[O:19][C:12]([CH2:11][C:10]#[N:14])=[N:13][CH:17]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

5

Edukt 3

HCID 8000Boron trifluoride etherateHCID 8010MalononitrileHCID 18667Diazoacetophenone

Produkt 1

HCID 126396202-(5-Phenyloxazol-2-yl)acetonitrileAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

BF3.Et2O (1.1 mL, 8.5 mmol) was added dropwise to a solution of malononitrile (2.26 g, 34.2 mmol) in dry CH2Cl2 (20 mL) at 0° C., followed by addition of 2-diazo-1-phenylethanone (0.5 g, 3.4 mmol) in DCM (5 mL). The reaction mixture was stirred at room temperature for 1 h and then quenched with aqueous 10% NaOH solution. The organic product was extracted with EtOAc and the combined extracts were washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica 60-120 mesh, eluant 5-10% EtOAc in petroleum ether) to get 2-(5-phenyloxazol-2-yl)acetonitrile (200 mg, yield 32%) as a brown solid. 1H NMR (300 MHz, CDCl3) δ 7.66-7.63 (m, 2H), 7.47-7.38 (m, 3H), 7.32 (s, 1H), 4.02 (s, 2H). MS (ESI) m/z: Calculated for C11H8N2O: 184.06. found: 185.2 (M+H)+.

Aufarbeitung

  1. customquenched with aqueous 10% NaOH solution
  2. extractionThe organic product was extracted with EtOAc
  3. washthe combined extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography (silica 60-120 mesh, eluant 5-10% EtOAc in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-1f6b58abba0e4f67b18d629d9db5ad84
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901156B2

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