Réaction #57437

Équation de réaction

N-hydroxylphthalimide

DBU

cyclohexylmethyl bromide

→

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

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Températurethe reaction was cooled to room temperature
2. 2
   Concentrationconcentrated to a red oil
3. 3
   AutreThe reaction was partitioned between ethyl acetate and 1N HCl
4. 4
   LavageThe organic layer was washed with saturated aqueous sodium bicarbonate solution, brine
5. 5
   Séchagedried over magnesium sulfate
6. 6
   AutreThe solvent was removed under vacuum
7. 7
   Autrethe crude product was triturated with hexanes providing 3.05 g (64%) of an off-white colored solid

Mode opératoire

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).

Source