Dimethylformamide → 2-Benzofurancarbonitrile

HRID 2269701Notes

Reaction equation

HRID 2269701 reaction equation
C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH2:21][C:22]#[N:23])=O>O>[O:20]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH:12]=[C:21]1[C:22]#[N:23]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 3863749(2-formylphenoxy)acetonitrile

Product 1

HCID 389502-BenzofurancarbonitrileYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate (65.2 g) was added to a DMF solution (500 ml) of (2-formylphenyl)oxyacetonitrile (38 g), which was stirred at 60° C. for 2.5 hours. Water was added to the reaction mixture, which was extracted with diethyl ether. The organic layer was washed with water and a saturated aqueous sodium chloride solution, then dried and concentrated. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10/1) to obtain the entitled compound (14.5 g).

Workup

  1. extractionwas extracted with diethyl ether
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, then dried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-e53149382d97478f886055c80c2dc03a
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

Loading…