Réaction #67583

Équation de réaction

2-Chloromethylpyridine hydrochloride

N-hydroxyphthalimide

triethylamine

→

N-(pyridine-2-ylmethoxy)phthalimide

Rendement 46.0%

Solvants

acetonitrile

ethyl acetate

Conditions de réaction

Traitement

1. 1
   Lavagewashed sequentially with 1N NaOH(aq), water, and brine
2. 2
   SéchageThe organic phase was dried over MgSO4
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated
5. 5
   AutreThe residue was recrystallized from ethyl acetate and hexanes

Mode opératoire

2-Chloromethylpyridine hydrochloride (514 mg, 3.13 mmol), N-hydroxyphthalimide (515 mg, 3.18 mmol), and triethylamine (1.3 mL, 9.3 mmol) were mixed in acetonitrile (5 mL) and stirred at 80° C. for 2.5 hours. The reaction mixture was diluted with ethyl acetate and washed sequentially with 1N NaOH(aq), water, and brine. The organic phase was dried over MgSO4, filtered, and concentrated. The residue was recrystallized from ethyl acetate and hexanes to provide N-(pyridine-2-ylmethoxy)phthalimide (364 mg, 1.44 mmol).

Source