Reacción #57437

Ecuación de reacción

N-hydroxylphthalimide

DBU

cyclohexylmethyl bromide

→

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

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente