Diethyl Ether → 2-Benzofurancarboxaldehyde, 5-methyl-
反応式
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]=1参加物
4
実験手順
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).
後処理
- temperaturethe reaction mixture was heated
- temperatureto reflux for 15 min
- additionwas added
- washthe mixture was washed with water and 10% aqueous KHCO3 solution
- dry with materialThe organic layer was then dried (MgSO4)
- concentrationconcentrated
- customthe residue was purified by column chromatography (silica gel; ethyl acetate/cyclohexane 4:1)
出典と根拠
- ORDレコード
- ord-85bbb2285ab140a498f0814691a80d66
- 出典データセット
- uspto-grants-2010_03
- 特許番号
- US07674815B2
反応ノート
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