反応 #502123

反応方程式

N-hydroxyphthalimide

K2CO3

tert-butyl bromoacetate

→

title compound

収率 71.0%

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

収率 71.0%

溶媒

DMF

反応条件

後処理

1. 1
   その他the solvent was evaporated under high vacuum
2. 2
   workup.DISSOLUTIONThe residue was dissolved in EtOAc
3. 3
   洗浄washed with brine
4. 4
   乾燥dried over Na2SO4
5. 5
   ろ過filtered
6. 6
   その他The residue after evaporation of the solvent
7. 7
   その他was recrystallized from a mixture of CH2Cl2/EtOAc/hexane

実験手順

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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