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

HRID 2388146노트

반응식

HRID 2388146 반응식
[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]

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-07b71e6733c74e4aa4e89b177b266bf0
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08269008B2

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