Potassium Carbonate → 6-Methoxy-2-benzofurancarbonitrile

HRID 2091012Notes

Reaction equation

HRID 2091012 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.Br[CH2:13][C:14]#[N:15].C(=O)([O-])[O-].[K+].[K+].N12CCCN=C1CCCCC2>CN(C)C=O.CC(C)=O>[CH3:11][O:10][C:8]1[CH:7]=[CH:6][C:3]2[CH:4]=[C:13]([C:14]#[N:15])[O:1][C:2]=2[CH:9]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 696002-Hydroxy-4-MethoxybenzaldehydeHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 130313696-Methoxy-2-benzofurancarbonitrileYield 47%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-hydroxy-4-methoxybenzaldehyde (10.0 g), bromoacetonitrile (5.04 mL) and acetone (100 mL) was added potassium carbonate (18.1 g), and the mixture was stirred at room temperature for 3 hr. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give a pale-brown solid. To a solution (100 mL) of the obtained solid in N,N-dimethylformamide was added 1,8-diazabicyclo[5.4.0]undec-7-ene (9.83 mL), and the mixture was stirred at 140° C. for 1.5 hr. The reaction mixture was concentrated under reduced pressure, 1N hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. Ethyl acetate was added to the residue, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:17, volume ratio) to give the title object compound (5.32 g, 47%) as a yellow solid.

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give a pale-brown solid
  4. stirringthe mixture was stirred at 140° C. for 1.5 hr
  5. concentrationThe reaction mixture was concentrated under reduced pressure, 1N hydrochloric acid
  6. additionwas added
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe extract was washed with saturated brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. additionEthyl acetate was added to the residue
  12. filtrationthe insoluble material was filtered off
  13. concentrationthe filtrate was concentrated under reduced pressure
  14. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:17, volume ratio)

Sources & evidence

ORD record
ord-156f7bda6969458684660645b8a67e60
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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