Ethanol → Ethyl 5-methyl-3-phenylisoxazole-4-carboxylate

HRID 2388146Notes

Reaction equation

HRID 2388146 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]([OH:15])=[O:14].S(Cl)(Cl)=O.[CH2:20](O)[CH3:21]>>[CH2:20]([O:14][C:13]([C:3]1[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:5][O:6][C:2]=1[CH3:1])=[O:15])[CH3:21]

Participants

4

Reactant 3

HCID 702EthanolHCID 143435-Methyl-3-phenylisoxazole-4-carboxylic acidHCID 24386Thionyl Chloride

Product 1

HCID 70838Ethyl 5-methyl-3-phenylisoxazole-4-carboxylate

Procedure

A mixture of 5-methyl-3-phenyl-isoxazole-4-carboxylic acid (10.0 g, 0.05 mol) and thionyl chloride (18.0 ml, 0.25 mol) in ethanol (100 ml) was refluxed for 5 h before it was cooled to room temperature and concentrated in vacuo. The residue was partitioned between ethyl acetate and water, the organic layer was washed with saturated aqueous sodium bicarbonate solution, and brine, before it was dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a yellow solid (10.24 g): 1H NMR (CDCl3, 200 MHz): δ=7.61 (m, 2H), 7.43 (m, 3H), 4.25 (q, J=7.0 Hz, 2H), 2.73 (s, 3H), 1.23 (t, J=7.0 Hz, 3H).

Workup

  1. temperaturewas refluxed for 5 h before it
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate and water
  4. washthe organic layer was washed with saturated aqueous sodium bicarbonate solution, and brine, before it
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-07b71e6733c74e4aa4e89b177b266bf0
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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