반응 #57429

반응 방정식

N-hydroxypthalimide

cyclopentylbromide

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

→

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

수율 80.2%

용매

dimethylformamide

반응 조건

후처리

1. 1
   온도After cooling to ambient temperature
2. 2
   기타the solvent was removed in vacuo
3. 3
   기타the residue was partitioned between ethyl acetate and 1N hydrochloric acid
4. 4
   기타After separating the phases
5. 5
   추출the aqueous layer was extracted again with ethyl acetate
6. 6
   세척The combined organic layers were washed with 5% w/v potassium carbonate, saturated aqueous brine
7. 7
   건조dried over anhydrous magnesium sulfate
8. 8
   여과filtered
9. 9
   기타evaporated in vacuo
10. 10
    기타The residue was triturated with hexane
11. 11
    여과filtered
12. 12
    기타dried under high vacuum

실험 절차

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).

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