Реакция #57437

Уравнение реакции

N-hydroxylphthalimide

DBU

cyclohexylmethyl bromide

→

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

Растворители

DMF

Условия реакции

Обработка

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

Методика

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).

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