تفاعل #57437

معادلة التفاعل

N-hydroxylphthalimide

DBU

cyclohexylmethyl bromide

→

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

المذيبات

DMF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر