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

HRID 444084Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 444084
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) were 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-a0fa72e87f6e4728928b95bea324cdf8
Quelldatensatz
uspto-grants-1981_04
Patentnummer
US04263037

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