Water → 1-(2-Cyanoethyl)-6-methoxyindan

HRID 1977997

Reaktionsgleichung

Reaktionsgleichung von HRID 1977997
Br[CH2:2][CH2:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[CH2:6][CH2:5]1.[C-:15]#[N:16].[Na+].O>CS(C)=O>[C:15]([CH2:2][CH2:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[CH2:6][CH2:5]1)#[N:16]

Komponenten

5

Edukt 3

HCID 962WaterHCID 8929Sodium CyanideHCID 110971511-(2-Bromoethyl)-6-methoxyindan

Produkt 1

HCID 109765261-(2-Cyanoethyl)-6-methoxyindanAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 1-(2-bromoethyl)-6-methoxyindan (1.75 g, 6.86 mmol) in dimethyl sulfoxide (80 ml) was added sodium cyanide (0.35 g, 7.20 mmol). This mixture was stirred for 40 minutes at 60° C. To the reaction mixture was added water, which was subjected to extraction with ethyl acetate. The extract solution was washed with brine and dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of a silica gel column chromatography (hexane/ethyl acetate, 85:15) to give 1.28 g (yield 93%) of the above-titled compound as an oily-product.

Aufarbeitung

  1. extractionwas subjected to extraction with ethyl acetate
  2. washThe extract solution was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationby distilling off the solvent under reduced pressure
  5. customThe residue was purified by means of a silica gel column chromatography (hexane/ethyl acetate, 85:15)

Quellen und Nachweise

ORD-Eintrag
ord-0b31ccfc063a4c8fa74faea8605d7839
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06235789B1

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