反応 #57437

反応方程式

N-hydroxylphthalimide

DBU

cyclohexylmethyl bromide

→

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

溶媒

DMF

反応条件

後処理

1. 1
   温度the reaction was cooled to room temperature
2. 2
   濃縮concentrated to a red oil
3. 3
   その他The reaction was partitioned between ethyl acetate and 1N HCl
4. 4
   洗浄The organic layer was washed with saturated aqueous sodium bicarbonate solution, brine
5. 5
   乾燥dried over magnesium sulfate
6. 6
   その他The solvent was removed under vacuum
7. 7
   その他the crude product was triturated with hexanes providing 3.05 g (64%) of an off-white colored solid

実験手順

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).

出典