Ethyl 5-(1-Hydroxyethyl)isoxazole-3-carboxylate → 5-Acetyl-isoxazole-3-carboxylic acid ethyl ester

HRID 2261348Notes

Reaction equation

HRID 2261348 reaction equation
[OH:1][CH:2]([C:4]1[O:8][N:7]=[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=1)[CH3:3]>O1CCOCC1.[O-2].[O-2].[Mn+4]>[C:2]([C:4]1[O:8][N:7]=[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=1)(=[O:1])[CH3:3]

Participants

4

Reactant 1

HCID 12920231Ethyl 5-(1-Hydroxyethyl)isoxazole-3-carboxylate

Product 1

HCID 27363535-Acetyl-isoxazole-3-carboxylic acid ethyl esterYield 88.9%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

4.06 g of ethyl 5-(1-hydroxyethyl)-isoxazole-3-carboxylate was dissolved in 100 ml of 1,4-dioxane, and 15.20 g of manganese dioxide was then added. The mixture was stirred and heated under reflux for 5 hours. The reaction mixture was cooled to room temperature and then filtered through Celite®. The filtrate was concentrated under reduced pressure to obtain 3.57 g of ethyl 5-acetylisoxazole-3-carboxylate.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 hours
  3. filtrationfiltered through Celite®
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4ec554f56f1b44cdbd044e7c5227977e
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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