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

HRID 2388146ノート

反応式

HRID 2388146 の反応式
[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]

参加物

4

反応物 3

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

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-07b71e6733c74e4aa4e89b177b266bf0
出典データセット
uspto-grants-2012_09
特許番号
US08269008B2

反応ノート

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