Dimethylformamide → HCID 10654815, compound

HRID 1384069Notes

Reaction equation

HRID 1384069 reaction equation
C([Li])CCC.[CH3:6][C:7]1[C:12]2[CH:13]=[CH:14][O:15][C:11]=2[C:10]([CH3:16])=[CH:9][CH:8]=1.CN(C)[CH:19]=[O:20].C(OCC)(=O)C>O1CCCC1>[CH3:6][C:7]1[C:12]2[CH:13]=[C:14]([CH:19]=[O:20])[O:15][C:11]=2[C:10]([CH3:16])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 331094,7-DimethylbenzofuranHCID 178418339Butyllithium

Product 1

HCID 10654815HCID 10654815, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a nitrogen atmosphere, n-butyllithium (1.56 M hexane solution, 18.4 ml) was added at −35° C. to a solution (50 ml) of the 4,7-dimethylbenzofuran (3.5 g) in dry tetrahydrofuran. Then the resulting mixture was stirred for 15 min and N,N-dimethylformamide (5.6 ml) was added dropwise to the mixture. Next, the reaction mixture was heated to room temperature and ethyl acetate was added to the mixture. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After evaporating the solvent, the resulting crude crystals were washed with n-hexane to give 4,7-dimethylbenzofuran-2-carbaldehyde (2.3 g) as a pale yellow solid.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customAfter evaporating the solvent
  4. washthe resulting crude crystals were washed with n-hexane

Sources & evidence

ORD record
ord-6974a5df6be44a4e8ad21c77bde84264
Source dataset
uspto-grants-2001_07
Patent number
US06258811B1

Reaction notes

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