Ethanol → Ethyl 5-ethoxy-4,5-dihydro-1,2-oxazole-3-carboxylate

HRID 1939642Notes

Reaction equation

HRID 1939642 reaction equation
[CH2:1]([O:3][CH:4]=[CH:5][C:6](=O)[C:7]([OH:9])=[O:8])[CH3:2].Cl.[NH2:12][OH:13].O.[CH2:15](O)[CH3:16]>>[CH2:1]([O:3][CH:4]1[O:13][N:12]=[C:6]([C:7]([O:9][CH2:15][CH3:16])=[O:8])[CH2:5]1)[CH3:2]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 54377377HCID 54377377, compound

Product 1

HCID 14811462Ethyl 5-ethoxy-4,5-dihydro-1,2-oxazole-3-carboxylateYield 76%

Procedure

17.22 g of 4-ethoxy-2-oxo-3-butenoic acid prepared according to the method of L. Tietze et al. (Lutz-F. Tietze, Heinrich Meier and Edgar Voss, Synthesis 1988, 274) are dissolved in 50 ml of anhydrous ethanol, and 7.34 g of hydroxylamine hydrochloride is added thereto, and the mixture is stirred at room temperature for 4 hours. The reaction mixture is added with water and extracted with methylene chloride. The organic layer is washed with water, dried, and evaporated. The resulting residue is distilled under reduced pressure to yield 14.3 g of ethyl 5-ethoxyisoxazoline-3carboxylate. (yield 76%)

Workup

  1. customTietze et al. (Lutz-F. Tietze, Heinrich Meier and Edgar Voss, Synthesis 1988, 274)
  2. extractionextracted with methylene chloride
  3. washThe organic layer is washed with water
  4. customdried
  5. customevaporated
  6. distillationThe resulting residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-f84e38c3b16b4d3cb563f12e8fb3a9b9
Source dataset
uspto-grants-1997_12
Patent number
US05696271

Reaction notes

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