Sodium Cyanide → 5-Cyano-2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran

HRID 1155954Notes

Reaction equation

HRID 1155954 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]([O:10][CH2:11][CH3:12])[C:7]([CH3:14])([CH3:13])[C:6]=2[CH:15]=1.[C-:16]#[N:17].[Na+]>CN(C)C=O.O>[C:16]([C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]([O:10][CH2:11][CH3:12])[C:7]([CH3:14])([CH3:13])[C:6]=2[CH:15]=1)#[N:17]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 205362435-Bromo-2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran

Product 1

HCID 205361845-Cyano-2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuranYield 97.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

5-Bromo-2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran (4.7 g, 0.017 mole) was heated under reflux with cuprous cyanide (2.7 g, 0.03 mole) in dimethyl formamide (10 ml) as in example 2 for 3 hours. A warm solution of sodium cyanide (5 g) in water (20 ml) was added with stirring and stirring was continued for 1 hour at ambient temperature. The solution was diluted with water and extracted with ether. The extracts were washed with water, dried over magnesium sulphate and run down yielding 3.6 g crude product. Purification was accomplished by silica gel chromatography in 1:4 ether/petroleum ether (b.p. 40°-60° C.). The yield of pure title product was 2.9 g (79%).

Workup

  1. stirringstirring
  2. extractionextracted with ether
  3. washThe extracts were washed with water
  4. dry with materialdried over magnesium sulphate

Sources & evidence

ORD record
ord-282d580e9b134d298131a9a25b250c74
Source dataset
uspto-grants-1982_06
Patent number
US04333759

Reaction notes

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