Potassium Cyanide → 2-(1-Benzothiophen-2-yl)acetonitrile

HRID 408563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 408563
Cl[CH2:2][C:3]1[S:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[CH:4]=1.[C-:12]#[N:13].[K+]>O1CCOCC1.O>[S:7]1[C:3]([CH2:2][C:12]#[N:13])=[CH:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]1=2

Komponenten

4

Edukt 2

HCID 9032Potassium CyanideHCID 128138372-(Chloromethyl)-1-benzothiophene

Produkt 1

HCID 126319232-(1-Benzothiophen-2-yl)acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Versuchsvorschrift

To a solution of 2-chloromethyl-benzo[b]thiophene (1 eq.) in dioxane/water (2/1) was added KCN (1.5 eq.). The reaction was refluxed for 4 h. The crude was partitioned between water and EtOAc. The organic layer was washed with water, then brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 95/5 to 90/10) to afford benzo[b]thiophen-2-yl-acetonitrile.

Aufarbeitung

  1. temperatureThe reaction was refluxed for 4 h
  2. customThe crude was partitioned between water and EtOAc
  3. washThe organic layer was washed with water
  4. dry with materialbrine, dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 95/5 to 90/10)

Quellen und Nachweise

ORD-Eintrag
ord-0ee2a227619148bfab509a57eefae68e
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759334B2

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