Dimethylformamide → 6-Methoxy-2-benzofurancarbonitrile

HRID 2269702Notes

Reaction equation

HRID 2269702 reaction equation
C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[CH:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=1[O:22][CH2:23][C:24]#[N:25])=O>O>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]2[CH:12]=[C:23]([C:24]#[N:25])[O:22][C:15]=2[CH:16]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 21794538HCID 21794538, compound

Product 1

HCID 130313696-Methoxy-2-benzofurancarbonitrileYield 49.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Potassium carbonate (15.1 g) and molecular sieves 4A (3 g) were added to a DMF solution (100 ml) of (2-formyl-5-methoxyphenyl)oxyacetonitrile (10.4 g), which was stirred at 100° C. for 10 hours. Water was added to the reaction mixture, which was extracted with ethyl acetate. 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 (ethyl acetate) to obtain the entitled compound (4.65 g).

Workup

  1. extractionwas extracted with ethyl acetate
  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 (ethyl acetate)

Sources & evidence

ORD record
ord-d3449691325f4259b0904c48b86516b3
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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