Aluminum isopropoxide → 3-(1-Hydroxybutyl)-5-[(2,4-dichlorophenoxy)methyl]-1,2,4-oxadiazole

HRID 4899

Reaction equation

HRID 4899 reaction equation
[CH2:1]([C:4]([C:6]1[N:10]=[C:9]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[O:8][N:7]=1)=[O:5])[CH2:2][CH3:3].CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-]>C(O)(C)C>[OH:5][CH:4]([C:6]1[N:10]=[C:9]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[O:8][N:7]=1)[CH2:1][CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 11143Aluminum isopropoxideHCID 197971373-Propylcarbonyl-5-[(2,4-dichlorophenoxy)methyl]-1,2,4-oxadiazole

Product 1

HCID 197971383-(1-Hydroxybutyl)-5-[(2,4-dichlorophenoxy)methyl]-1,2,4-oxadiazoleYield 54%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

0.316 g of 3-propylcarbonyl-5-[(2,4-dichlorophenoxy)methyl]-1,2,4-oxadiazole and 0.20 g of aluminum isopropoxide were added to 10 ml of isopropanol. The mixture was heated to reflux for 48 hours. After evaporation of isopropanol, water was added to the residue. The aqueous solution was extracted with ethylacetate. After evaporation of ethylacetate, the residue was purified by column chromatography(hexane: ethylacetate=3:2) to provide 0.17 g of the desired product(yield: 54.0%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 48 hours
  3. customAfter evaporation of isopropanol, water
  4. additionwas added to the residue
  5. extractionThe aqueous solution was extracted with ethylacetate
  6. customAfter evaporation of ethylacetate
  7. customthe residue was purified by column chromatography(hexane: ethylacetate=3:2)

Sources & evidence

ORD record
ord-71d372ee817748b9b806f8449f71356b
Source dataset
uspto-grants-1993_09
Patent number
US05242890

Linked notes

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