Benzophenone → 3,3-Diphenylacrylonitrile

HRID 2190323

Reaktionsgleichung

Reaktionsgleichung von HRID 2190323
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[C:14]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[C:15]1([C:14]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:5][C:3]#[N:4])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

5

Edukt 3

HCID 3102BenzophenoneHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonate

Produkt 1

HCID 2743523,3-Diphenylacrylonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of sodium hydride (60% wt in mineral oil) (0.780 g, 32.5 mmol) in THF (100 mL) at room temperature was added diethyl cyanomethylphosphonate (4.50 g, 25.4 mmol) (4 mL). The mixture was stirred for 30 min and benzophenone (4.22 g, 23.2 mmol) was added. The reaction mixture was stirred at room temperature for 1d, and partially concentrated, diluted with Et2O, washed with water (1×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 5% to 20% EtOAc in hexanes) gave 3,3-diphenylacrylonitrile.

Aufarbeitung

  1. concentrationpartially concentrated
  2. additiondiluted with Et2O
  3. washwashed with water (1×), brine (1×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash column chromatography on silica gel (eluted with 5% to 20% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-2db76fdc3678418482438b285bd433dd
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324396B2

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