Hydrochloric Acid → HCID 21990147, Verbindung

HRID 2377179Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2377179
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][OH:12])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[OH-].[K+].[C:15](#[N:18])[CH:16]=[CH2:17].Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.O>[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][O:12][CH2:17][CH2:16][C:15]#[N:18])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 7855AcrylonitrileHCID 14797Potassium HydroxideHCID 119833712-(1-Benzothiophen-5-yl)ethan-1-ol

Produkt 1

HCID 21990147HCID 21990147, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

To 2.00 g of 2-(1-benzothiophen-5-yl)-1-ethanol were added 13 mg of potassium hydroxide, 36 mg of tetra-n-butylammonium bromide and 1.11 mL of acrylonitrile, and the resulting mixture was stirred at 45° C. for 3 hours. After the reaction mixture was cooled, water and ethyl acetate were added thereto and the pH was adjusted to 1 with 2 mol/L hydrochloric acid. The insoluble materials were removed and then the organic layer was separated. The organic layer was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was purified by a column chromatography (eluent; hexane:ethyl acetate=3:1) to obtain 2.46 g of 3-[2-(1-benzothiophen-5-yl)ethoxy]propiono-nitrile as a colorless oil.

Aufarbeitung

  1. temperatureAfter the reaction mixture was cooled
  2. customThe insoluble materials were removed
  3. customthe organic layer was separated
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue was purified by a column chromatography (eluent; hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-0095d39e4fdb429cb8e598fe4bf98d78
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07468443B2

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