反応 #74005

反応方程式

tert-butyl 3-(2-(2-(2-(tosyloxy)ethoxy)ethoxy)ethoxy)propanoate

potassium phthalimide

water

→

tert-butyl 3-(2-(2-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)ethoxy)ethoxy)propanoate

収率 80.0%

溶媒

DMF

反応条件

後処理

1. 1
   その他Into a 250-mL round-bottom flask purged
2. 2
   温度maintained with an inert atmosphere of nitrogen
3. 3
   その他The DMF was removed under vacuum
4. 4
   その他to afford a brown oil residue
5. 5
   抽出the mixture was extracted with 3×50 mL of ethyl acetate
6. 6
   洗浄The combined organic layers were washed with saturated brine
7. 7
   乾燥dried over anhydrous sodium sulfate
8. 8
   その他After evaporation of solvent
9. 9
   その他The solvent was removed from fractions
10. 10
    workup.ADDITIONcontaining phthalimide
11. 11
    洗浄the residue was washed with 20% ethyl acetate/petroleum ether

実験手順

Into a 250-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of tert-butyl 3-(2-(2-(2-(tosyloxy)ethoxy)ethoxy)ethoxy)propanoate (13.4 g, 30.98 mmol, 1.00 equiv) in anhydrous DMF (100 mL) followed by potassium phthalimide (7.5 g, 40.49 mmol, 1.31 equiv). The resulting solution was heated to 100° C. and stirred for 3 h. The reaction progress was monitored by LCMS. The DMF was removed under vacuum to afford a brown oil residue. To the residue was added 200 mL water and the mixture was extracted with 3×50 mL of ethyl acetate. The combined organic layers were washed with saturated brine and dried over anhydrous sodium sulfate. After evaporation of solvent. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (0˜1:3). The solvent was removed from fractions containing phthalimide and the residue was washed with 20% ethyl acetate/petroleum ether to yield 10.1 g (78%) of tert-butyl 3-(2-(2-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)ethoxy)ethoxy)propanoate as pale yellow oil.

出典