반응 #57437

반응 방정식

N-hydroxylphthalimide

DBU

cyclohexylmethyl bromide

→

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

용매

DMF

반응 조건

후처리

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

실험 절차

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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