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

HRID 1772369Notes

Reaction equation

HRID 1772369 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-8833e097da8842c1922d07de0b753016
Source dataset
uspto-grants-2016_02
Patent number
US09249161B2

Reaction notes

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