Reaktion #62562

Reaktionsgleichung

aniline

furan

→

2-phenylfuran

Ausbeute 39.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe mixture was then washed with water and saturated NaCl solution
2. 2
   Trocknendried over anhydrous Na2SO4
3. 3
   Sonstigeevaporated
4. 4
   FiltrationThe brown residue was filtered through a short column of neutral alumina (activity grade II)
5. 5
   Einengenconcentrated
6. 6
   workup.DISTILLATIONthe residue distilled in vacuo

Vorschrift

A solution of aniline (12.5 g, 0.134M) and i-amylnitrite (27.5 ml, 0.205M) in furan (400 ml) was stirred at 30° C. (bath temperature) for 24 hours under N2. The mixture was then washed with water and saturated NaCl solution, dried over anhydrous Na2SO4 and evaporated. The brown residue was filtered through a short column of neutral alumina (activity grade II) using pentane as an eluent. The fractions were combined and concentrated and the residue distilled in vacuo to give pure 2-phenylfuran (7.65 g, 39% yield), bp 51°-54° C. (1.0 mm). NMR (CDCl3) δ 6.45 ppm (dd, 1H, J=1.5, 3.0 Hz, furan-H4), 6.62 (d, 1H, J=4.0 Hz, furan-H3), 7.2-7.8 (m, 6H, phenyl and furan-H5).

Quelle