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

HRID 1155958Notes

Reaction equation

HRID 1155958 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) 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.

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-05851cca75ed44b6b94e4f50bfea1166
Source dataset
uspto-grants-1982_06
Patent number
US04333759

Reaction notes

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