Reaktion #57436

Reaktionsgleichung

N-hydroxylphthalimide

DBU

2-bromobutane

→

yellow solid

Ausbeute 89.0%

2-(sec-butoxy)-1H-isoindole-1,3(2H)-dione

Ausbeute 89.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction was cooled to room temperature
2. 2
   Einengenconcentrated to a red oil
3. 3
   SonstigeThe reaction was partitioned between ethyl acetate and 1N HCl
4. 4
   WaschenThe organic layer was washed with saturated aqueous sodium bicarbonate solution
5. 5
   workup.DISTILLATIONdistilled water, brine
6. 6
   Trocknendried over magnesium sulfate
7. 7
   SonstigeThe solvent was removed under vacuum

Vorschrift

N-hydroxylphthalimide (18.4 mmol, 3.0 g) was dissolved in anhydrous DMF (20 mL) under nitrogen. To the stirring solution, DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) (27.6 mmol, 4.13 mL) was injected followed by 2-bromobutane (22.1 mmol, 2.41 mL) and the reaction was warmed to 55° C. After stirring for 18 hour, the reaction was cooled to room temperature and concentrated to a red oil. The reaction was partitioned between ethyl acetate and 1N HCl. The organic layer was washed with saturated aqueous sodium bicarbonate solution, distilled water, brine and dried over magnesium sulfate. The solvent was removed under vacuum providing 3.57 g (89%) of a yellow solid. Rf: 0.8 (2:1 hexanes/ethyl acetate); H1-NMR (CDCl3): δ 7.80 (2H,m), 7.73 (2H,m), 4.31 (1H,m), 1.81 (1H,m), 1.64 (1H,m), 1.32 (3H,d), 1.03 (3H,t).

Quelle