N,6-dimethoxy-N-methyl-2-benzofurancarboxamide → 2-Benzofurancarboxaldehyde, 6-methoxy-
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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° .