Hydrochloric Acid → HCID 11075305, Verbindung

HRID 749597Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 749597
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([CH:6]=[C:7]([C:10]#[N:11])[C:8]#[N:9])=[CH:4][CH:3]=1.[CH:14]([Mg]Br)([CH3:16])[CH3:15].Cl>O1CCCC1.[Cu]I>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([CH:7]([C:8]#[N:9])[C:10]#[N:11])[CH:14]([CH3:16])[CH3:15])=[CH:12][CH:13]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 158474-ChlorobenzalmalononitrileHCID 178418365HCID 178418365, Verbindung

Produkt 1

HCID 11075305HCID 11075305, VerbindungAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Lösungsmittel

Versuchsvorschrift

First, 1.02 g of (4-chlorobenzylidene)malononitrile was dissolved in 20 ml of tetrahydrofuran, to which a catalytic amount of copper (I) iodide was added, and while stirring under ice cooling, a solution of isopropyl magnesium bromide in tetrahydrofuran (prepared from 0.34 g of magnesium, 10 ml of tetrahydrofuran, and 1.46 ml of isopropyl bromide) was added dropwise, followed by stirring for 30 minutes under ice cooling. Then, 10% hydrochloric acid was added to the reaction mixture, which became acidic and was extracted with ethyl 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 0.66 g of (1-(4-chlorophenyl)-2-methylpropyl)malononitrile (the intermediate (3)).

Aufarbeitung

  1. additionwas added
  2. stirringby stirring for 30 minutes under ice cooling
  3. extractionwas extracted with ethyl 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-ad0ec5f19fc54c8b9bd10f11159bc849
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07402691B2

Notizen zur Reaktion

Wird geladen…