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

HRID 548982

Reaction equation

HRID 548982 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-ac3f40c2faa7422a8e9aaa0d2bc845a9
Source dataset
uspto-grants-2011_05
Patent number
US07943634B2

Linked notes

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