تفاعل #502123

معادلة التفاعل

N-hydroxyphthalimide

K2CO3

tert-butyl bromoacetate

→

title compound

المردود 71.0%

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

المردود 71.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىthe solvent was evaporated under high vacuum
2. 2
   workup.DISSOLUTIONThe residue was dissolved in EtOAc
3. 3
   غسيلwashed with brine
4. 4
   تجفيفdried over Na2SO4
5. 5
   ترشيحfiltered
6. 6
   أخرىThe residue after evaporation of the solvent
7. 7
   أخرىwas recrystallized from a mixture of CH2Cl2/EtOAc/hexane

الإجراء التجريبي

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.

المصدر