反応 #1596043

反応方程式

2-(4-nitrophenyl)acetamide

1,3-dioxol-2-one

Eaton's Reagent

→

title compound

収率 25.0%

2-(4-nitrobenzyl)oxazole

収率 25.0%

溶媒

反応条件

後処理

1. 1
   温度After this time, the reaction was cooled
2. 2
   抽出extracted with ethyl acetate
3. 3
   乾燥The combined organic layer was dried over anhydrous sodium sulfate
4. 4
   ろ過filtered
5. 5
   濃縮the filtrate was concentrated
6. 6
   その他The residue was purified by column chromatography (silica, dichloromethane/methanol)

実験手順

A mixture of 2-(4-nitrophenyl)acetamide (1.0 g, 5.55 mmol), 1,3-dioxol-2-one (0.955 g, 11.10 mmol), and Eaton's Reagent (9.9 g, 34.97 mmol) was heated to 100° C. overnight under a nitrogen atmosphere. After this time, the reaction was cooled, diluted with ice water, and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, dichloromethane/methanol) to afford the title compound (0.250 g, 25%). MW=204.18. 1H NMR (DMSO-d6, 500 MHz) δ 8.26-8.18 (m, 2H), 8.05 (d, J=0.8 Hz, 1H), 7.57 (d, J=8.8 Hz, 2H), 7.16 (s, 1H), 4.34 (s, 2H); APCI MS m/z 205 [M+H]+.

出典