3,5-Dimethoxyisonicotinaldehyde → 3-Hydroxy-5-methoxyisonicotinaldehyde
反応式
C[O:2][C:3]1[CH:10]=[N:9][CH:8]=[C:7]([O:11][CH3:12])[C:4]=1[CH:5]=[O:6].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[OH:2][C:3]1[CH:10]=[N:9][CH:8]=[C:7]([O:11][CH3:12])[C:4]=1[CH:5]=[O:6]参加物
4
実験手順
To a solution of 3,5-dimethoxyisonicotinaldehyde (2.7 g, 16.16 mmol, 1 eq.) in DCM (100 mL) was added AlCl3 (4.31 g, 32.32 mmol, 2.0 eq.) at rt. The mixture was reflux O/N, cooled to rt, and added into ice (200 g). The aqueous layer was extracted with DCM three times. The combined organic layers were dried over Na2SO4, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give 3-hydroxy-5-methoxyisonicotinaldehyde (420 mg, 17%) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 10.96 (s, 1H), 10.26 (s, 1H), 7.96 (s, 1H), 7.80 (s, 1H), 3.84 (s, 3H). LRMS (M+H+) m/z 154.1.
後処理
- temperatureThe mixture was reflux O/N
- extractionThe aqueous layer was extracted with DCM three times
- dry with materialThe combined organic layers were dried over Na2SO4
- concentrationconcentrated
- custompurified on silica gel using
- additiona mixture of EtOAc and hexanes as eluent
出典と根拠
- ORDレコード
- ord-9575f126ac8744a49dbb82a94e6911d1
- 出典データセット
- uspto-grants-2015_04
- 特許番号
- US09012450B2
反応ノート
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