Dimethylformamide → 5-Cyano-2-acetoxy-2,3-dihydro-3,3-dimethylbenzofuran

HRID 1155958Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1155958
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]([O:10][C:11](=[O:13])[CH3:12])[C:7]([CH3:15])([CH3:14])[C:6]=2[CH:16]=1.[CH3:17][N:18](C)C=O.[C-]#N.[Na+]>O>[C:17]([C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]([O:10][C:11](=[O:13])[CH3:12])[C:7]([CH3:15])([CH3:14])[C:6]=2[CH:16]=1)#[N:18]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 205361885-Bromo-2,3-dihydro-3,3-dimethyl-2-acetoxybenzofuran

Produkt 1

HCID 205362085-Cyano-2-acetoxy-2,3-dihydro-3,3-dimethylbenzofuran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

The product from stage (a) (4 g), cuprous cyanide (1.8 g) and dimethylformamide (10 ml) was boiled under reflux with stirring for three hours. The mixture was then cooled, and a solution of sodium cyanide (4.5 g) in water (18 ml) was added. After stirring for 1 hour, the product was extracted into ether, the ethereal extract being washed with water (twice), dried over magnesium sulphate, and run down. Recrystallisation of the residue from ethanol gave 1.8 g of pure product, mp 140°-142° C.

Aufarbeitung

  1. temperatureunder reflux
  2. temperatureThe mixture was then cooled
  3. stirringAfter stirring for 1 hour
  4. extractionthe product was extracted into ether
  5. extractionthe ethereal extract
  6. washbeing washed with water (twice),
  7. dry with materialdried over magnesium sulphate
  8. customRecrystallisation of the residue from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-05851cca75ed44b6b94e4f50bfea1166
Quelldatensatz
uspto-grants-1982_06
Patentnummer
US04333759

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