Reacción #502123

Ecuación de reacción

N-hydroxyphthalimide

K2CO3

tert-butyl bromoacetate

→

title compound

Rendimiento 71.0%

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

Rendimiento 71.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe solvent was evaporated under high vacuum
2. 2
   workup.DISSOLUTIONThe residue was dissolved in EtOAc
3. 3
   Lavadowashed with brine
4. 4
   Secadodried over Na2SO4
5. 5
   Filtraciónfiltered
6. 6
   OtroThe residue after evaporation of the solvent
7. 7
   Otrowas recrystallized from a mixture of CH2Cl2/EtOAc/hexane

Procedimiento

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.

Fuente