反応 #10754

反応方程式

3-Benzo[b]thiophen-2-yl-2-hydroxy-4-methoxy-benzaldehyde

potassium carbonate

Methyl iodide

→

3-benzo[b]thiophen-2-yl-2,4-dimethoxy-benzaldehyde

収率 97.1%

溶媒

acetone

反応条件

後処理

1. 1
   温度the solution was heated
2. 2
   温度to reflux for 3.5 h
3. 3
   温度After cooling
4. 4
   その他the crude reaction
5. 5
   workup.ADDITIONmix
6. 6
   濃縮was concentrated on the rotavap
7. 7
   workup.ADDITIONmix of saturated, aqueous NH4Cl to water
8. 8
   抽出extracted with EtOAc (2×15 mL)
9. 9
   乾燥The organic phase was dried over sodium sulfate
10. 10
    ろ過filtered
11. 11
    濃縮concentrated

実験手順

Ex-44B: 3-Benzo[b]thiophen-2-yl-2-hydroxy-4-methoxy-benzaldehyde (Ex-44A, 57.4 mg, 0.202 mmol) was dissolved in acetone (5 mL) and potassium carbonate (31 mg, 0.22 mmol) was added. Methyl iodide (25 uL, 0.40 mmol) was added and the solution was heated to reflux for 3.5 h. After cooling, the crude reaction mix was concentrated on the rotavap. The resulting residue was taken up in 10 mL of a 1:9 mix of saturated, aqueous NH4Cl to water and extracted with EtOAc (2×15 mL). The organic phase was dried over sodium sulfate, filtered, and concentrated to provide 58.5 mg of 3-benzo[b]thiophen-2-yl-2,4-dimethoxy-benzaldehyde as an orange, oily residue which was used without further purification, 97% yield. 1H-NMR (CDCl3) δ 10.31 (s, 1H), 7.92 (d, J=9 Hz, 1H), 7.81–7.88 (m, 2H), 7.56 (d, 1H), 7.33–7.39 (m, 2H), 6.88 (d, J=9 Hz, 1H), 3.91 (s, 3H), 3.64 (s, 3H).

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