Reaction #4994

Reaction equation

3-ethylcarbonyl-5-[(2,4-dichlorophenoxy)methyl]-1,2,4-oxadiazole

hydroxyamine hydrochloride

→

desired product

Yield 85.0%

3-(alpha-hydroxyiminopropyl)-5-[(2,4-dichlorophenoxy)methyl]-1,2,4-oxadiazole

Yield 85.0%

Solvents

methanol

Conditions

Workup

1. 1
   TemperatureThe mixture was heated
2. 2
   Temperatureto reflux for 4 hours
3. 3
   OtherAfter evaporation of methanol, water
4. 4
   workup.ADDITIONwas added to the residue
5. 5
   ExtractionThe aqueous solution was extracted with ethylacetate
6. 6
   OtherAfter evaporation of ethylacetate
7. 7
   Otherthe residue was purified by column chromatography(benzene:ether=1.1)

Procedure

0.9 g of 3-ethylcarbonyl-5-[(2,4-dichlorophenoxy)methyl]-1,2,4-oxadiazole and 0.21 g of hydroxyamine hydrochloride were added to 10 ml of methanol. The mixture was heated to reflux for 4 hours. After evaporation of methanol, water was added to the residue. The aqueous solution was extracted with ethylacetate. After evaporation of ethylacetate, the residue was purified by column chromatography(benzene:ether=1.1) to provide 0.80 g of the desired product(yield: 85.0%).

Source