Water → 3-(6-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-propionitrile

HRID 420196Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 420196
[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]([CH2:20][CH2:21]OS(C)(=O)=O)[CH2:15][CH2:14][CH2:13]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C-:27]#[N:28].[K+].[I-].[K+].O>CN(C=O)C>[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]([CH2:20][CH2:21][C:27]#[N:28])[CH2:15][CH2:14][CH2:13]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 4875Potassium IodideHCID 9032Potassium CyanideHCID 59021717Methanesulfonic acid 2-(6-benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-ethyl ester

Produkt 1

HCID 590217743-(6-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-propionitrileAusbeute 96,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of methanesulfonic acid 2-(6-benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-ethyl ester (1.21 g, 3.07 mmol), potassium cyanide (0.799 g, 12.27 mmol) and potassium iodide (0.25 g) in 50 mL of DMF was heated to 95° C. under argon with stirring for 24 hours. The reaction mixture was cooled and poured into 500 mL of water. The aqueous mix was extracted three times with EtOAc, and the combined organic phases were washed with water, saturated brine, and dried (MgSO4). Evaporation of the solvent under reduced pressure gave an oil that was purified by elution on silica gel (hexanes:EtOAc 1:1). Removal of the solvent under reduced pressure yielded 0.950 g (2.97 mmol, 95.1% of 3-(6-benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-propionitrile as a white crystalline solid. MS: 326 (M+H)+.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. additionThe aqueous mix
  3. extractionwas extracted three times with EtOAc
  4. washthe combined organic phases were washed with water, saturated brine
  5. dry with materialdried (MgSO4)
  6. customEvaporation of the solvent under reduced pressure
  7. customgave an oil that
  8. customwas purified by elution on silica gel (hexanes:EtOAc 1:1)
  9. customRemoval of the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8c542ddae77344fd9ef71055c0b77474
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093424B2

Notizen zur Reaktion

Wird geladen…