Hydrochloric Acid → (4-(Trifluoromethyl)benzyl)malononitrile

HRID 749598

Reaktionsgleichung

Reaktionsgleichung von HRID 749598
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:14]=[CH:13][C:6]([CH:7]=[C:8]([C:11]#[N:12])[C:9]#[N:10])=[CH:5][CH:4]=1.[BH4-].[Na+].Cl>C(O)C>[F:1][C:2]([F:15])([F:16])[C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH:8]([C:11]#[N:12])[C:9]#[N:10])=[CH:13][CH:14]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 714296(4-(Trifluoromethyl)benzylidene)malononitrileHCID 4311764Sodium borohydride

Produkt 1

HCID 10656743(4-(Trifluoromethyl)benzyl)malononitrileAusbeute 51,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

First, 4.44 g of (4-(trifluoromethyl)benzylidene)malononitrile was dissolved in 20 ml of ethanol, and while stirring at room temperature, a suspension of 0.19 g of sodium borohydride in 5 ml of ethanol was added dropwise, followed by stirring at room temperature for 30 minutes. Then, 10% hydrochloride acid was added to the reaction mixture, which became acidic and was extracted with diethyl ether. The organic layer was successively washed with 10% hydrochloric acid, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2.30 g of (4-(trifluoromethyl)benzyl)malononitrile (the intermediate (4)).

Aufarbeitung

  1. additionwas added dropwise
  2. stirringby stirring at room temperature for 30 minutes
  3. extractionwas extracted with diethyl ether
  4. washThe organic layer was successively washed with 10% hydrochloric acid
  5. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d8439fc2695e4fb0b52aae099c3403eb
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07402691B2

Verknüpfte Notizen

Wird geladen…