反应 #57429

反应方程式

N-hydroxypthalimide

cyclopentylbromide

1,8-diazabicyclo[5.4.0]undec-7-ene

→

2-(cyclopentyloxy)-1H-isoindole-1,3(2H)-dione

收率 80.2%

溶剂

dimethylformamide

反应条件

后处理

1. 1
   温度After cooling to ambient temperature
2. 2
   其他the solvent was removed in vacuo
3. 3
   其他the residue was partitioned between ethyl acetate and 1N hydrochloric acid
4. 4
   其他After separating the phases
5. 5
   萃取the aqueous layer was extracted again with ethyl acetate
6. 6
   洗涤The combined organic layers were washed with 5% w/v potassium carbonate, saturated aqueous brine
7. 7
   干燥dried over anhydrous magnesium sulfate
8. 8
   过滤filtered
9. 9
   其他evaporated in vacuo
10. 10
    其他The residue was triturated with hexane
11. 11
    过滤filtered
12. 12
    其他dried under high vacuum

实验过程

A mixture of N-hydroxypthalimide (10.00 g, 61.3 mmol), cyclopentylbromide (8.21 mL, 76.63 mmol), and 1,8-diazabicyclo[5.4.0]undec-7-ene (13.75 mL, 76.6 mmol) were combined under an Argon atmosphere in dimethylformamide (50 mL). The mixture was heated to 55° C. and stirred vigorously for 1.5 hours. After cooling to ambient temperature, the solvent was removed in vacuo and the residue was partitioned between ethyl acetate and 1N hydrochloric acid. After separating the phases, the aqueous layer was extracted again with ethyl acetate. The combined organic layers were washed with 5% w/v potassium carbonate, saturated aqueous brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The residue was triturated with hexane, filtered, and dried under high vacuum to provide 2-(cyclopentyloxy)-1H-isoindole-1,3(2H)-dione (11.37 g, 80%). H1-NMR (chloroform-D3): 1.61 (m, 2H), 1.77 (m, 2H), 1.97 (m, 4H), 4.91 (m, 1H), 7.73 (m, 2H), 7.82 (m, 2H). MS(ESI): 254 (M+Na).

来源