반응 #10754

반응 방정식

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

수율 97.1%

용매

acetone

반응 조건

후처리

1. 1
   온도the solution was heated
2. 2
   온도to reflux for 3.5 h
3. 3
   온도After cooling
4. 4
   기타the crude reaction
5. 5
   workup.ADDITIONmix
6. 6
   농축was concentrated on the rotavap
7. 7
   workup.ADDITIONmix of saturated, aqueous NH4Cl to water
8. 8
   추출extracted with EtOAc (2×15 mL)
9. 9
   건조The organic phase was dried over sodium sulfate
10. 10
    여과filtered
11. 11
    농축concentrated

실험 절차

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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