Реакция #69688

Уравнение реакции

potassium iodide

1-(2-Bromo-ethoxy)-2-methoxy-ethane

4-hydroxy-2-(4-methoxy-benzyl)-isoindole-1,3-dione

potassium carbonate

1-(2-bromo-ethoxy)-2-methoxy-ethane

→

title compound

Выход 73.0%

2-(4-Methoxy-benzyl)-4-[2-(2-methoxy-ethoxy)-ethoxy]-isoindole-1,3-dione

Выход 73.0%

Растворители

DMF

Условия реакции

Обработка

1. 1
   workup.WAITAfter a further 17 hours
2. 2
   workup.WAITAfter 3 hours
3. 3
   Температураthe mixture maintained at 60° C. for a further 20 hours
4. 4
   КонцентрированиеThe mixture was concentrated in vacuo
5. 5
   Промывкаwashed with potassium carbonate solution and brine
6. 6
   СушкаThe organic phase was dried (MgSO4)
7. 7
   Концентрированиеconcentrated

Методика

1-(2-Bromo-ethoxy)-2-methoxy-ethane (107 mg, 0.58 mmol) was added to a suspension of 4-hydroxy-2-(4-methoxy-benzyl)-isoindole-1,3-dione (150 mg, 0.53 mmol) and potassium carbonate (200 mg, 1.4 mmol) in DMF (2 mL). After 3.5 hours, a catalytic amount of potassium iodide was added. After a further 17 hours, the mixture was warmed to 60° C. After 3 hours, an additional amount of 1-(2-bromo-ethoxy)-2-methoxy-ethane (20 mg, 0.11 mmol) was added and the mixture maintained at 60° C. for a further 20 hours. The mixture was concentrated in vacuo then the residue was taken up in ethyl acetate and washed with potassium carbonate solution and brine. The organic phase was dried (MgSO4) and concentrated to give the title compound as a yellow oil (149 mg, 73%). 1H NMR (methanol-d4) 7.71 (1H, t), 7.43-7.40 (2H, m), 7.31-7.27 (2H, m), 6.87-6.83 (2H, m), 4.71 (2H, s), 4.37-4.34 (2H, m), 3.92-3.89 (2H, m), 3.77-3.74 (5H, m), 3.55-3.53 (2H, m), 3.33 (3H, s). MS:

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