Reaktion #57429

Reaktionsgleichung

N-hydroxypthalimide

cyclopentylbromide

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

→

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

Ausbeute 80.2%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to ambient temperature
2. 2
   Sonstigethe solvent was removed in vacuo
3. 3
   Sonstigethe residue was partitioned between ethyl acetate and 1N hydrochloric acid
4. 4
   SonstigeAfter separating the phases
5. 5
   Extraktionthe aqueous layer was extracted again with ethyl acetate
6. 6
   WaschenThe combined organic layers were washed with 5% w/v potassium carbonate, saturated aqueous brine
7. 7
   Trocknendried over anhydrous magnesium sulfate
8. 8
   Filtrationfiltered
9. 9
   Sonstigeevaporated in vacuo
10. 10
    SonstigeThe residue was triturated with hexane
11. 11
    Filtrationfiltered
12. 12
    Sonstigedried under high vacuum

Vorschrift

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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