Cyanoacetic acid → (7-Methoxy-1-benzofuran-3-yl)acetonitrile

HRID 1091844Notes

Reaction equation

HRID 1091844 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[O:10][CH2:9][C:8](=O)[C:7]=2[CH:6]=[CH:5][CH:4]=1.[C:13]([CH2:15]C(O)=O)#[N:14].C([O-])(=O)C.[NH4+]>C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3]1[C:11]2[O:10][CH:9]=[C:8]([CH2:15][C:13]#[N:14])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 9740Cyanoacetic acidHCID 517165Ammonium AcetateHCID 28181127-Methoxybenzofuran-3(2H)-one

Product 1

HCID 15618729(7-Methoxy-1-benzofuran-3-yl)acetonitrileYield 30%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

The solution of 7-methoxy-1-benzofuran-3(2H)-one (reference) (7.5 g, 0.046 mol), cyanoacetic acid (19.55 g, 0.23 mol) and ammonium acetate (7.08 g, 0.092 mol) in xylene was refluxed for 16-18 h. using dean stark apparatus. Xylene was removed under diminished pressure. Brown black residue was taken in ethyl acetate, washed with water and concentrated. On purification on silica gel it yielded (7-methoxy-1-benzofuran-3-yl)acetonitrile (30%).

Workup

  1. customXylene was removed under diminished pressure
  2. washwashed with water
  3. concentrationconcentrated
  4. customOn purification on silica gel it

Sources & evidence

ORD record
ord-8c6ce5e83fbe45a1bfd00fde849a74c2
Source dataset
uspto-grants-2012_03
Patent number
US08129401B2

Reaction notes

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