Réaction #57429

Équation de réaction

N-hydroxypthalimide

cyclopentylbromide

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

→

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

Rendement 80.2%

Solvants

dimethylformamide

Conditions de réaction

Traitement

1. 1
   TempératureAfter cooling to ambient temperature
2. 2
   Autrethe solvent was removed in vacuo
3. 3
   Autrethe residue was partitioned between ethyl acetate and 1N hydrochloric acid
4. 4
   AutreAfter separating the phases
5. 5
   Extractionthe aqueous layer was extracted again with ethyl acetate
6. 6
   LavageThe combined organic layers were washed with 5% w/v potassium carbonate, saturated aqueous brine
7. 7
   Séchagedried over anhydrous magnesium sulfate
8. 8
   Filtrationfiltered
9. 9
   Autreevaporated in vacuo
10. 10
    AutreThe residue was triturated with hexane
11. 11
    Filtrationfiltered
12. 12
    Autredried under high vacuum

Mode opératoire

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).

Source