تفاعل #57429

معادلة التفاعل

N-hydroxypthalimide

cyclopentylbromide

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

→

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

المردود 80.2%

المذيبات

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter cooling to ambient temperature
2. 2
   أخرىthe solvent was removed in vacuo
3. 3
   أخرىthe residue was partitioned between ethyl acetate and 1N hydrochloric acid
4. 4
   أخرىAfter separating the phases
5. 5
   استخلاصthe aqueous layer was extracted again with ethyl acetate
6. 6
   غسيلThe combined organic layers were washed with 5% w/v potassium carbonate, saturated aqueous brine
7. 7
   تجفيفdried over anhydrous magnesium sulfate
8. 8
   ترشيحfiltered
9. 9
   أخرىevaporated in vacuo
10. 10
    أخرىThe residue was triturated with hexane
11. 11
    ترشيحfiltered
12. 12
    أخرىdried under high vacuum

الإجراء التجريبي

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).

المصدر