Ethanol → Ethyl 2-(3-methylisoxazol-5-yl)acetate

HRID 2401425Notes

Reaction equation

HRID 2401425 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7][C:8]([OH:10])=[O:9])[O:4][N:3]=1.[CH3:11][CH2:12]O.OS(O)(=O)=O>>[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[O:4][N:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 41955322-(3-Methyl-1,2-oxazol-5-yl)acetic acid

Product 1

HCID 11593502Ethyl 2-(3-methylisoxazol-5-yl)acetateYield 97.3%

Procedure

To a solution of 2-(3-methylisoxazol-5-yl)acetic acid (7.28 g, 51.6 mmol) in EtOH (200 mL, 3425 mmol) was added concentrated H2SO4 (0.30 mL, 5.63 mmol) at room temperature. After 48 h, the reaction mixture was concentrated in vacuo to give a dark brown oil. The crude ester was filtered over a plug of silica (50 g) and the product was eluted with 40% Et2O:60% Hexanes (400 mL). The filtrate was subsequently concentrated to give the product ethyl 2-(3-methylisoxazol-5-yl)acetate (8.50 g, 50.2 mmol, 97% yield) as a clear oil. LC/MS m/z 170 [M+H]+.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customto give a dark brown oil
  3. filtrationThe crude ester was filtered over a plug of silica (50 g)
  4. washthe product was eluted with 40% Et2O
  5. concentrationThe filtrate was subsequently concentrated

Sources & evidence

ORD record
ord-a6e7ca9cd3bf41e0b6101287b4fdc531
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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