Diethyl Ether → 2-Benzofurancarboxaldehyde, 5-methyl-
Reaction equation
C[O:2][CH:3](OC)[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:7]=1[CH:8]=O.CCOCC>FC(F)(F)C(O)=O>[CH3:14][C:11]1[CH:12]=[CH:13][C:6]2[O:5][C:4]([CH:3]=[O:2])=[CH:8][C:7]=2[CH:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
154 mg (0.69 mmol) of 2-(2,2-dimethoxy-ethoxy)-5-methyl-benzaldehyde were dissolved in trifluoroacetic acid and the reaction mixture was heated to reflux for 15 min. After cooling to RT ether was added and the mixture was washed with water and 10% aqueous KHCO3 solution. The organic layer was then dried (MgSO4) and concentrated and the residue was purified by column chromatography (silica gel; ethyl acetate/cyclohexane 4:1) to yield 76 mg (48%) of 5-methyl-benzofuran-2-carbaldehyde as brown oil. 1HNMR (CDCl3, 300 MHz): δ 2.47 (s, 3H), 7.34 (d, J=8.7 Hz, 1H), 7.50 (m, 3H), 9.85 (s, 1H).