Reaktion #57437

Reaktionsgleichung

N-hydroxylphthalimide

DBU

cyclohexylmethyl bromide

→

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

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, brine
5. 5
   Trocknendried over magnesium sulfate
6. 6
   SonstigeThe solvent was removed under vacuum
7. 7
   Sonstigethe crude product was triturated with hexanes providing 3.05 g (64%) of an off-white colored solid

Vorschrift

N-hydroxylphthalimide (18.4 mmol, 3.0 g) was dissolved in anhydrous DMF (20 mL) under nitrogen. To the stirring solution, DBU (27.6 mmol, 4.13 mL) was injected followed by cyclohexylmethyl bromide (23.0 mmol, 3.21 mL) and the reaction was warmed to 55° C. After stirring for 15 hours, 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, brine and dried over magnesium sulfate. The solvent was removed under vacuum, and the crude product was triturated with hexanes providing 3.05 g (64%) of an off-white colored solid. H1-NMR (CDCl3): δ 7.80 (2H,m), 7.73(2H,m), 3.98 (2H,d), 2.03-1.65 (5H,m), 1.31-1.03 (6H,m).

Quelle