Реакция #502123

Уравнение реакции

N-hydroxyphthalimide

K2CO3

tert-butyl bromoacetate

→

title compound

Выход 71.0%

tert-Butyl 2-(1,3-dioxobenzo(c)azolin-2-yloxy)acetate

Выход 71.0%

Растворители

DMF

Условия реакции

Обработка

1. 1
   Другоеthe solvent was evaporated under high vacuum
2. 2
   workup.DISSOLUTIONThe residue was dissolved in EtOAc
3. 3
   Промывкаwashed with brine
4. 4
   Сушкаdried over Na2SO4
5. 5
   Фильтрацияfiltered
6. 6
   ДругоеThe residue after evaporation of the solvent
7. 7
   Другоеwas recrystallized from a mixture of CH2Cl2/EtOAc/hexane

Методика

A mixture of N-hydroxyphthalimide (10 g, 61.3 mmol), K2CO3 (16.9 g, 122 mmol) and tert-butyl bromoacetate (12 g, 9 mL, 61.3 mmol) in DMF (60 mL) was stirred at room temperature for 3 hours and the solvent was evaporated under high vacuum. The residue was dissolved in EtOAc, washed with brine, dried over Na2SO4 and filtered. The residue after evaporation of the solvent was recrystallized from a mixture of CH2Cl2/EtOAc/hexane to give the title compound (12 g, 71% yield) as a white solid. Mp 140-141° C. 1H NMR (300 MHz, CDCl3) δ 7.80-7.90 (m, 2H), 7.74-7.77 (m, 2H), 4.71 (s, 2H), 1.49 (s, 9H). 13C NMR (75 MHz, CDCl3) δ 166.0, 163.0, 134.7, 128.9, 123.7, 83.0, 73.5, 28.1. Mass spectrum (API-TIS) m/z 278 (MH−), 295 (MNH4+). Anal. calcd. for C14H15NO5: C, 60.64; H, 5.45; N, 5.05. Found C, 60.47; H, 5.31; N, 4.96.

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