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

HRID 444084Notes

Reaction equation

HRID 444084 reaction equation
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]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 20536188HCID 20536188, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a0fa72e87f6e4728928b95bea324cdf8
Source dataset
uspto-grants-1981_04
Patent number
US04263037

Reaction notes

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