반응 #58919

반응 방정식

2-(4-nitrophenyl)acetohydrazide

trimethyl orthobutyrate

methanesulfonic acid

tetrahydrofuran

→

2-(4-nitrobenzyl)-5-propyl-1,3,4-oxadiazole

용매

Water

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도under reflux for 2 hrs
3. 3
   추출the mixture was extracted with ethyl acetate
4. 4
   세척The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
5. 5
   건조dried over anhydrous magnesium sulfate
6. 6
   농축concentrated

실험 절차

A mixture of 2-(4-nitrophenyl)acetohydrazide (7.0 g), trimethyl orthobutyrate (16.01 g), methanesulfonic acid (0.69 g) and tetrahydrofuran (200 mL) was heated under reflux for 2 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and 2-(4-nitrobenzyl)-5-propyl-1,3,4-oxadiazole was obtained as a colorless oil (7.73 g, yield 87%) from a fraction eluted with hexane-ethyl acetate (3:2-1:2, v/v).

출처