Hydroxyamine hydrochloride → Ethyl 5-(2-furyl)isoxazole-3-carboxylate

HRID 606278Notes

Reaction equation

HRID 606278 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5](=O)[CH2:6][C:7]([C:9]1[O:10][CH:11]=[CH:12][CH:13]=1)=[O:8])[CH3:2].Cl.[NH2:17]O>>[CH2:1]([O:3][C:4]([C:5]1[CH:6]=[C:7]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[O:8][N:17]=1)=[O:15])[CH3:2]

Participants

3

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 3006753Ethyl 4-(furan-2-yl)-2,4-dioxobutanoate

Product 1

HCID 7127810Ethyl 5-(2-furyl)isoxazole-3-carboxylateYield 77%

Conditions

Temperature
85 °C

Procedure

After a suspension of 10.0 g of 4-furan-2-yl-2,4-dioxo-butyric ethyl ester prepared above and hydroxylamine hydrochloride was stirred at 85° C. for 2 hrs, the solvent was removed under reduced pressure. The concentrate was dissolved in a mixture of methylene chloride and distilled water, followed by separating the organic layer. The organic layer was dried over anhydrous sodium sulfate, filtered through a silica gel layer, and concentrated in vacuo to produce a yield of 8.01 g of 5-furan-2-yl-isoxazole-3-carboxylic acid ethyl ester (Yield 77%). The concentrate was used in the next step without further purification.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe concentrate was dissolved in a mixture of methylene chloride
  3. distillationdistilled water
  4. customby separating the organic layer
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered through a silica gel layer
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-007cb13f59aa45389f162263289d67b0
Source dataset
uspto-grants-2011_03
Patent number
US07915297B2

Reaction notes

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