Dimethylformamide → HCID 10654815, compound

HRID 277174Notes

Reaction equation

HRID 277174 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

18.4 ml n-butyl lithium (1.56 M solution in hexane) was added to 50 ml solution of 3.5 g 4,7-dimethylbenzofuran in anhydrous tetrahydrofuran at −35° C. in a nitrogen atmosphere. After stirring for 15 minutes,5.6 ml N,N-dimethylformamide was added dropwise thereto, and the temperature was raised to room temperature. Ethyl acetate was added to the reaction mixture, and the organic layer was washed with brine and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting crude crystals were washed with n-hexane to give 2.3 g of 4,7-dimethylbenzofuran-2-carbaldehyde as apale yellow solid.

Workup

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

Sources & evidence

ORD record
ord-c4d8e4f73b004d48b88619140d9445fc
Source dataset
uspto-grants-2002_03
Patent number
US06355669B1

Reaction notes

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