2-Bromopropane → 3-Methyl-2-(2-naphthyl)butyronitrile

HRID 1071606Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1071606
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]#[N:13].Br[CH:15]([CH3:17])[CH3:16].[OH-].[K+]>CS(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[Na+].O>[CH3:16][CH:15]([CH3:17])[CH:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[C:12]#[N:13]

Komponenten

7

Edukt 3

HCID 63582-BromopropaneHCID 14797Potassium HydroxideHCID 820082-Naphthylacetonitrile

Produkt 1

HCID 223937393-Methyl-2-(2-naphthyl)butyronitrileAusbeute 64,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

3.00 g (17.9 mmol) of 2-naphthylacetonitrile was dissolved in 10 ml of dimethyl sulfoxide, and 2.43 g (19.7 mmol) of 2-bromopropane, 330 mg (0.90 mmol, cat) of tetra-n-butylammonium iodide and 10 ml of 50% potassium hydroxide were successively added thereto. After completion of the reaction, brine was added, and the mixture was extracted with ether. The organic layer was washed with brine, dried over magnesium sulfate and evaporated, to give a crude product. The crude product was subjected to 150 g of silica gel (ethyl acetate:hexane=1:10), to give 2.42 g (11.6 nmol, 64.6%) of the title compound as a yellow oil.

Aufarbeitung

  1. additionwas added
  2. extractionthe mixture was extracted with ether
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto give a crude product

Quellen und Nachweise

ORD-Eintrag
ord-de92b22fc5124d0eb36d9b9a5af07a2e
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06906072B1

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