N,6-dimethoxy-N-methyl-2-benzofurancarboxamide → 2-Benzofurancarboxaldehyde, 6-methoxy-

HRID 128730Notes

Reaction equation

HRID 128730 reaction equation
CON(C)[C:4]([C:6]1[O:7][C:8]2[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:9]=2[CH:10]=1)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:16][O:15][C:13]1[CH:12]=[CH:11][C:9]2[CH:10]=[C:6]([CH:4]=[O:5])[O:7][C:8]=2[CH:14]=1

Participants

4

Reactant 2

HCID 19374960N,6-dimethoxy-N-methyl-2-benzofurancarboxamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 409082-Benzofurancarboxaldehyde, 6-methoxy-Yield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An ice-cooled solution of 4.0 g (0.017 mole) of N,6-dimethoxy-N-methyl-2-benzofurancarboxamide in 100 ml of tetrahydrofuran was treated cautiously over 15 minutes (under a nitrogen atmosphere) with 0.65 g (0.017 mole) of lithium aluminum hydride. The mixture was stirred for 1 hour, then quenched by the careful addition of 100 ml of saturated aqueous sodium bisulfate solution. The reaction mixture was extracted with ether (3X 75 ml), and the combined extracts were washed with cold 2% aqueous hydrochloric acid (2X 100 ml), followed by brine (lX 100 ml). The organic layer was dried (anhydrous magnesium sulfate) and evaporated. The residue was chromatographed (silica gel, dichloromethane elution) to yield 2.2 g (74% yield) of the analytically pure aidehyde, mp 75°-77° .

Workup

  1. customquenched by the careful addition of 100 ml of saturated aqueous sodium bisulfate solution
  2. extractionThe reaction mixture was extracted with ether (3X 75 ml)
  3. washthe combined extracts were washed with cold 2% aqueous hydrochloric acid (2X 100 ml)
  4. dry with materialThe organic layer was dried (anhydrous magnesium sulfate)
  5. customevaporated
  6. customThe residue was chromatographed
  7. wash(silica gel, dichloromethane elution)
  8. customto yield 2.2 g (74% yield) of the analytically pure aidehyde, mp 75°-77°

Sources & evidence

ORD record
ord-0ef30c163b124da78b27308867f774b6
Source dataset
uspto-grants-1995_11
Patent number
US05464856

Reaction notes

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