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

HRID 2388146Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2388146
[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]

Komponenten

4

Edukt 3

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

Produkt 1

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

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-07b71e6733c74e4aa4e89b177b266bf0
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08269008B2

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