반응 #80821

반응 방정식

2-ethoxalylmethylcarbonylquinoline

→

2-acetylquinoline

수율 96.1%

용매

hydrochloric acid

반응 조건

후처리

1. 1
   농축concentrated in vacuo
2. 2
   workup.DISSOLUTIONThe residue was dissolved in aqueous sodium bicarbonate
3. 3
   추출extracted with ethyl acetate
4. 4
   세척The extract was washed with water and brine
5. 5
   건조dried over magnesium sulfate
6. 6
   농축concentrated
7. 7
   기타The residue was purified by silica gel column chromatography with 20:1 to 7:1 hexane/ethyl acetate

실험 절차

A solution of 2-ethoxalylmethylcarbonylquinoline (32.24 g, 0.132 mol) in concentrated hydrochloric acid (300 mL) was refluxed for 4 h and concentrated in vacuo. The residue was dissolved in aqueous sodium bicarbonate and extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with 20:1 to 7:1 hexane/ethyl acetate to give 21.72 g of 2-acetylquinoline (96%): 1H NMR (270 MHz, CDCl3) δ8.25 (d, 1H, J=8.6 Hz), 8.19 (dd, 1H, J=8.3, 1 Hz), 8.13 (d, 1H, J=8.6 Hz), 7.86 (dd, 1H, J=8.3, 1 Hz), 7.78 (td, 1H, J=8.3, 1 Hz), 7.64 (td, 1H, J=8.3, 1 Hz), 2.87 (s, 3H).

출처