تفاعل #69688

معادلة التفاعل

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

المردود 73.0%

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

المردود 73.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   workup.WAITAfter a further 17 hours
2. 2
   workup.WAITAfter 3 hours
3. 3
   درجة الحرارةthe mixture maintained at 60° C. for a further 20 hours
4. 4
   تركيزThe mixture was concentrated in vacuo
5. 5
   غسيلwashed with potassium carbonate solution and brine
6. 6
   تجفيفThe organic phase was dried (MgSO4)
7. 7
   تركيزconcentrated

الإجراء التجريبي

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:

المصدر